Dichloromethane → 2-amino-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one

HRID 1893897Notes

Reaction equation

HRID 1893897 reaction equation
[NH2:1][C:2]1[N:3]=[C:4]([CH3:15])[C:5]2[CH:11]=[CH:10][C:9](=[O:12])[N:8]([CH2:13][CH3:14])[C:6]=2[N:7]=1.ClCCl.[Br:19]Br>CC(C)=O>[NH2:1][C:2]1[N:3]=[C:4]([CH3:15])[C:5]2[CH:11]=[C:10]([Br:19])[C:9](=[O:12])[N:8]([CH2:13][CH3:14])[C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 24408BromineHCID 161230622-amino-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one

Product 1

HCID 576069632-amino-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Amino-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one (2.70 g, 13.2 mmol) was added to dichloromethane (100 mL), and then bromine (0.75 mL, 1.10 equiv.) was added slowly. This reaction mixture was stirred for 3 h at room temperature. After that, the solvent was evaporated nearly 80% volume of reaction mixture under vacuum, and then acetone was added to give 3.54 g 2-Amino-6-bromo-8-ethyl-4-methylpyrido[2,3-d]pyrimidin-7(8H)-one as a tan solid. LC/MS: Calculated for C10H11BrN4O (283.12). Found: 285.15 (M+2). HPLC analytical purity: 97.7%.

Workup

  1. customAfter that, the solvent was evaporated nearly
  2. custom80% volume of reaction mixture under vacuum

Sources & evidence

ORD record
ord-90206497df764c0f96492285db153793
Source dataset
uspto-grants-2013_08
Patent number
US08513266B2

Reaction notes

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