Water → 2-Phenylimidazo[1,2-c]pyrimidin-7-amine

HRID 908236

Reaction equation

HRID 908236 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1)=O.C([O-])(O)=O.[Na+].[NH2:16][C:17]1[CH:22]=[C:21]([NH2:23])[N:20]=[CH:19][N:18]=1.O>CO>[C:5]1([C:3]2[N:16]=[C:17]3[CH:22]=[C:21]([NH2:23])[N:20]=[CH:19][N:18]3[CH:2]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6259Phenacyl bromideHCID 79608Pyrimidine-4,6-diamineHCID 516892Sodium Bicarbonate

Product 1

HCID 4040512-Phenylimidazo[1,2-c]pyrimidin-7-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

ω-Bromoacetophenone (9.04 g, 45 mmol) and NaHCO3 (4.30 g, 50 mmol) were added to a solution of 4,6-diaminopyrimidine (5.00 g, 0.45 mmol) in methanol (80 ml), and the mixture was heated to reflux (3 h). Upon cooling, water (40 ml) was added, and the suspension was stirred at r.t. (15 min). The precipitated title compound (5.62 g, 59%) was isolated by filtration, washed with small amounts of water and methanol, and dried under vacuum. MS (m/e)=211.1 [M+H+].

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux (3 h)
  3. temperatureUpon cooling
  4. customThe precipitated title compound (5.62 g, 59%)
  5. customwas isolated by filtration
  6. washwashed with small amounts of water and methanol
  7. customdried under vacuum

Sources & evidence

ORD record
ord-977e643049e748a8ae969dd88ddb423f
Source dataset
uspto-grants-2011_09
Patent number
US08017604B2

Linked notes

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