2,4-Diaminopyrimidine → HCID 58446906, compound

HRID 1958340Notes

Reaction equation

HRID 1958340 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][CH:8]=[C:7]([F:11])[CH:6]=1)=O.[NH2:12][C:13]1[N:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]=1>CC(C)=O>[F:11][C:7]1[CH:6]=[C:5]([C:3]2[N:12]=[C:13]3[N:18]=[C:17]([NH2:19])[CH:16]=[CH:15][N:14]3[CH:2]=2)[CH:10]=[CH:9][CH:8]=1

Participants

4

Reactant 2

HCID 674312,4-DiaminopyrimidineHCID 27374513-Fluorophenacyl bromide

Product 1

HCID 58446906HCID 58446906, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

2-Bromo-1-(3-fluorophenyl)ethanone (10.9 g, 50 mmol) was added to a solution of 2,4-diaminopyrimidine (3.70 g, 34 mmol) in acetone (185 ml), and the mixture was heated to reflux for 6 h. The cooled suspension was filtered and the precipitate was washed with acetone (50 ml). The solid was re-suspended in water (35 ml) and NH4OHaq. (25%, 50 ml), then it was collected over a glass fiber paper and the filtrate was washed with H2O (75 ml). After drying under vacuum, the product was obtained (5.56 g, 72%) as a yellow solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureto reflux for 6 h
  3. filtrationThe cooled suspension was filtered
  4. washthe precipitate was washed with acetone (50 ml)
  5. custom(25%, 50 ml), then it was collected over a glass fiber paper
  6. washthe filtrate was washed with H2O (75 ml)
  7. customAfter drying under vacuum
  8. customthe product was obtained (5.56 g, 72%) as a yellow solid

Sources & evidence

ORD record
ord-4a74ac3f78ff4e1ba896fe4f67489d71
Source dataset
uspto-grants-2013_04
Patent number
US08410117B2

Reaction notes

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