7-chlorothiazolo[5,4-d]pyrimidine

b. A solution of S-amino--chloropyrimidine^-thiol (49) (4 gm, 24.75 mmol) in triethylorthoformate was heated to reflux for 1 h. The reaction mixture was concentrated to 60percent of the original volume and cooled in a refrigerator. The solid obtained was collected by filtration and dried in vacuum to furnish 7-chlorothiazolo[5, 4-d]pyrimidine (50) (2.8 g, 66.04 percent) as a tan solid.A mixture of 5-amino-6- chloropyrimidine-4-thiol (1.6 g, 10 mmol) in triethoxymethane (30 mL) was refluxed for 1 h. It was cooled to rt and the brown crystal was collected by filtration and to give 0.90 g of the title compound (53percent). 7-Chlorothiazolo[5, 4-d]pyrimidine (100.0 mg, 0.58 mmol), 2-(4-nitrophenyl)ethan-1-amine hydrochloride (118.0 mg, 0.58 mmol) and Et3N (244.0 muL, 1.75 mmol) were added toi-PrOH (5.8 mL). The reaction mixture was stirred at room temperature for 22 hours. After addition of water, the reaction mixture was extracted with EtOAc, washed with brine, dried with Na2SO4, filtered and distilled under reduced pressure. The residue was purified by C18 reversed-phase silica gel column chromatography (CH3CN:H2O condition) and freeze-dried to obtain the yellow solid compound, N-(4-nitrophenethyl)thiazolo[5, 4-d]pyrimidin-7-amine (124.0 mg, 71%).[750][751]1H NMR (400 MHz, DMSO-d6) delta = 9.25 (s, 1H), 8.42 (s, 2H), 8.16 (d, J= 8.7 Hz, 2H), 7.55 (d, J= 8.6 Hz, 2H), 3.81 (q, J= 6.8 Hz, 2H), 3.11 (t, J= 7.1 Hz, 2H)[752]LC/MS ESI (+): 302 (M+1)7-Chlorothiazolo[5, 4-d]pyrimidine (1.00 g, 5.54 mmol) was dissolved in EtOH (5.17 mL). DIPEA (2.30 mL, 13.2 mmol) was added, followed by QS, 2R, 4R)-4- amino-2-(hydroxymethyl)cyclopentanol hydrochloride (1.40 g, 8.40 mmol). The reaction mixture was heated under microwave irradiation at 125 C for 20 min. The reaction mixture was concentrated and the crude compound was purified by silica gel chromatography (0-15% MeOH in DCM) to provide Intermediate 65 (1.10g, 75%), LCMS (AA): m/z = 267.0 (M+H).A mixture of 7-Chlorothiazolo[5, 4-d]pyrimidine (50 mg, 0.29 mmol), 5-fluoroindoline (42 mg, 0.31 mmol), 4M HCI in dioxane (0.075 ml) in IPA (0.7ml) were irradiated in the microwave at 100 C for 30 mm. The precipitate was filtered and washed with methanol. The residuewas purified by filtration through an aminopropyl cartridge eluting with DCM:MeOH (10:1) to give a green solid (23 mg, 27%). 1H NMR (400 MHz, DM50-cl6) 6 ppm 3.29 (t, J=8.47 Hz, 2 H), 4.74 - 4.92 (m, 2 H), 7.08 (td, J9.16, 2.75 Hz, I H), 7.15 - 7.26 (m, I H), 8.61 (dd, J8.93, 4.81 Hz, I H), 8.64 (s, I H), 9.34 (s, I H).

Molecular Weight:171.61
XLogP3:2
Hydrogen Bond Acceptor Count:4
Exact Mass:170.9657959
Monoisotopic Mass:170.9657959
Topological Polar Surface Area:66.9
Heavy Atom Count:10
Complexity:134
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes