1H-Pyrrolo[2,3-d]pyrimidin-2-amine(9CI)

To a suspension of 2-AMINO-4- CHLORO-7H-PYRROLO [2, 3-d] pyrimidine (1) (1.0 g, 6.0 mmol) in MeOH (50 mL) and aqueous ammonium hydroxide (1 mL) was added 10percent Pd-C (500 mg). The reaction mixture was stirred under atmospheric pressure for 17 h and the catalyst was filtered through A pad of Celite. The filtrate was concentrated and chromatographed with silica gel (CH2CL2 : MEOH = 90: 10) to yield 717 mg of the target compound (90percent). H NMR (DMSO-D6) : 8 11.4 (bs, 1H), 8. 50 (s, 1 H), 7.11 (dd, J= 3. 6, 0. 6 HZ, 1H), 6.49 (bs, 2H), 6.32 (dd, J= 3. 6, 0. 9 HZ, 1 H).To a suspension of 2-AMINO-4- CHLORO-7H-PYRROLO [2, 3-d] pyrimidine (1) (1.0 g, 6.0 mmol) in MeOH (50 mL) and aqueous ammonium hydroxide (1 mL) was added 10percent Pd-C (500 mg). The reaction mixture was stirred under atmospheric pressure for 17 h and the catalyst was filtered through A pad of Celite. The filtrate was concentrated and chromatographed with silica gel (CH2CL2 : MEOH = 90: 10) to yield 717 mg of the target compound (90percent). H NMR (DMSO-D6) : 8 11.4 (bs, 1H), 8. 50 (s, 1 H), 7.11 (dd, J= 3. 6, 0. 6 HZ, 1H), 6.49 (bs, 2H), 6.32 (dd, J= 3. 6, 0. 9 HZ, 1 H).The final product 03 (20 mg, 0.062 mmol), 2-amino-7H-pyrrolo [2, 3-d] pyrimidine (25 mg, 0.186 mmol) and Et3N (25 mg, 0.25 mmol) were weighed into a bottle, Add 2 mL of DMF to dissolve the reaction reagent.The reaction was heated at 50 C overnight.The crude reaction product was directly purified by reverse-phase HPLC to obtain the target compound YC124 (18.8 mg).Step 1: To a stirred solution of 7H-pyrroio[2, 3-d]pyrimidin-2-amine (500 mg, 3.73 mmoi) in acetonitrile (9 mL) and dichloromethane (9 mL) was added Boc-anhydride (2.85 g, 13.1 inmol) and DMAP (91 trig, 0.75 rnmoi). The reaction mixture was stirred overnight. Themixture was concentrated under reduced pressure, and the residue was purified by column chromatography on silica (0-40% EtOAc in Hex) to afford 2-methyi-2-propanyi 2-(bis{[(2- methyl-2-propanyl)oxy] carbonyi} amino)-7H-pyrroio[2, 3-d]pyrimidine-7-carboxylate, MS: 435 (M+1). (134 mg, 1.00 mmol), QD32 (576 mg, 1.56 mmol), potassium carbonate(415 mg, 3.00 mmol) and proline(23 mg, 0.2 mmol) It was added to an eggplant type flask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (19 mg, 0.1 mmol) was added and the reaction solution was deoxygenated.Heat to 90 C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over celite. The targetcompound was obtained in 130 mg. (198 mg, 1.48 mmol), QD27 (682 mg, 1.84 mmol), potassium carbonate(621 mg, 4.50 mmol) and valine (35 mg, 0.3 mmol) it was added to an eggplant type flask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (29 mg, 0.15 mmol) was added and the reaction solution was deoxygenated. Heat to 90C and stir for 16 hours. After the reaction was completed, it was cooledto room temperature, water and ethyl acetate were added, and the mixture was filtered over Celite. The target compound was obtained in an amount of 120 mg. (198 mg, 1.48 mmol), QD04 (550 mg, 1.56 mmol), potassium carbonate(621 mg, 4.50 mmol) and proline (35 mg, 0.3 mmol) It was added to an eggplant type flask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (29 mg, 0.15 mmol) was added and the reactionsolution was deoxygenated. Heat to 90 C and stir for 16 hours. After the reaction was completed, it was cooledto room temperature, water and ethyl acetate were added, and the mixture was filtered over Celite. The target compound was obtained in an amount of 350 mg. (134 mg, 1.00 mmol), 1-bromo-2, 4-difluoro-5-iodobenzene (636 mg, 2.00 mmol), potassium carbonate (415 mg) , 3.00 mmol) and proline(23 mg, 0.2 mmol) were added to an eggplant type flask, and dimethyl sulfoxide was added thereto, and the reaction solution was deoxidized. Copper iodide (19 mg, 0.1 mmol) was added and the reaction solution was deoxygenated. Heat to 90C and stir for 16hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over Celite. The target compound was obtained in 306 mg. (198 mg, 1.48 mmol), QD07 (530 mg, 1.49 mmol), potassium carbonate(621 mg, 4.50 mmol) and proline (35 mg, 0.3 mmol) It was added to an eggplant type flask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (29 mg, 0.15 mmol) was added and the reaction solution was deoxygenated. Heat to 90C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over Celite. The target compound was obtained in 130 mg. (134 mg, 1.00 mmol), 2-bromo-5-fluoro-4-iodopyridine (604 mg, 2.00mmol), potassium carbonate (415 mg, 3.00 mmol) and proline (23 mg, 0.2 mmol) was added to the eggplant flask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (19 mg, 0.1 mmol) was added and the reaction solution was deoxygenated. Heat to 90 C and stir for 16 hours. After the reactionwas completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over celite. The target compound was obtained in 246 mg. (134 mg, 1.00 mmol), 2-bromo-4-iodo-1-toluene (600 mg, 2.00 mmol), potassium carbonate (415 mg, 3.00 mmol) and proline (23 mg, 0.2 mmol) was added to the eggplant flask, dimethyl sulfoxide was added, and the reaction solution was deoxidized. Copper iodide (19 mg, 0.1 mmol) was added and the reaction solution was deoxygenated. Heat to 90 C and stir for 16 hours. After the reaction was completed, it was cooled to room temperature, water and ethyl acetate were added, and the mixture was filtered over celite. The target compound was obtained in an amount of 200 mg.

Molecular Weight:134.14
XLogP3:0.3
Hydrogen Bond Donor Count:2
Hydrogen Bond Acceptor Count:3
Exact Mass:134.059246208
Monoisotopic Mass:134.059246208
Topological Polar Surface Area:67.6
Heavy Atom Count:10
Complexity:127
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes