4-Amino-5-bromopyrimidine

A variation of a published procedure7 was followed: 4- Aminopyrimidine (1.00 g, 10.5 mmol, 1.0 equiv) and CaCO3 (263 mg, 2.63 mmol, 0.25 equiv) were combined in H2O (20 mL) and Br2 (1.06 mL, 20.5 mmol, 2.0 equiv) was added dropwise. The reaction mixture was stirred at 60 °C for 45 minutes, cooled to room temperature, and then poured into CH2Cl2 (20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2 × 20 mL). The combined organic layers were set aside. The aqueous layer was treated with 20percent aqueous K2CO3 until pH 9-10 was achieved, and the product precipitated. The precipitate was removed via filtration and dried, affording the product (1.08 g, 6.22 mmol, 59percent) as a light tan solid.A mixture of To a solution of 179 (260 mg, 1.5 mrnoi) in DMF (4 niL) is added tributyi(i ethoxyvinyl)tin (543 111g. 1, 5 mrnoi) and Pd(dppf)C12 (110 mg, 0.15 mmol). After stirring at 100 C for 16 hours, the mixture is cooled to room temperature, filtered, concentrated, and purified by silica gel column chromatography (MeOH:DCM == 1:50) to give 180 as a brown solid (30 rng, 15% yield). (MS: [M±H I 3& 1)General procedure: Step 1: A vial equipped with a magnetic stir bar was charged with the ortho-haloaminopyridine and BrettPhos G1 precatalyst (6 mol %). The vial was sealed with a teflon screw cap, and evacuated and backfilled with argon three times. The amine (1 to 1.5 mol eq) was added via syringe, followed by LiHMDS solution (1M in THF, 2.5 mol eq). Amines that were solid at room temperature were added with the catalyst. The reaction mixture was stirred at 40 C for 4-18 h, until LC/MS indicated complete conversion of the starting material. The mixture was cooled to room temperature, diluted with dichloromethane, and poured into water. The organic phase was separated and the aqueous phase was extracted twice more with dichloromethane. The combined organic phases were dried over Na2SO4. The solvent was removed under reduced pressure.A variation of a published procedure7 was followed: 4- Aminopyrimidine (1.00 g, 10.5 mmol, 1.0 equiv) and CaCO3 (263 mg, 2.63 mmol, 0.25 equiv) were combined in H2O (20 mL) and Br2 (1.06 mL, 20.5 mmol, 2.0 equiv) was added dropwise. The reaction mixture was stirred at 60 C for 45 minutes, cooled to room temperature, and then poured into CH2Cl2 (20 mL). The layers were separated and the aqueous layer was extracted with CH2Cl2 (2 × 20 mL). The combined organic layers were set aside. The aqueous layer was treated with 20% aqueous K2CO3 until pH 9-10 was achieved, and the product precipitated. The precipitate was removed via filtration and dried, affording the product (1.08 g, 6.22 mmol, 59%) as a light tan solid.

Molecular Weight:174.00
XLogP3:0.5
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:3
Exact Mass:172.95886
Monoisotopic Mass:172.95886
Topological Polar Surface Area:51.8
Heavy Atom Count:8
Complexity:77.7
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes