Carbonic acid-guanidine (1:1) → 2-Amino-4-phenylpyrimidine

HRID 1355685Notes

Reaction equation

HRID 1355685 reaction equation
CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)=O.C(=O)(O)O.[NH2:18][C:19]([NH2:21])=[NH:20].C[O-].[Na+]>CO>[NH2:20][C:19]1[N:21]=[C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[CH:4]=[CH:3][N:18]=1

Participants

5

Reactant 3

HCID 286947Carbonic acid-guanidine (1:1)HCID 3534603-(Dimethylamino)-1-phenyl-2-propen-1-oneHCID 10942334Sodium Methoxide

Product 1

HCID 5987772-Amino-4-phenylpyrimidineYield 82%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a stirred solution of 3.0 g (17.1 mmol) 3-(dimethylamino)acrylophenone and 10.2 g (56.5 mmol) guanidine carbonate in 50 ml methanol was added 21.2 ml (114 mmol) sodium methylate (5.4M in methanol) and the mixture heated at reflux for 3 hours. The reaction mixture was then concentrated in vacuo. On addition of 50 ml water, a precipitate appeared which was collected by filtration and washed sequentially with water and ether to afford 2.4 g (82%) 2-amino-4-phenylpyrimidine as a crystalline solid. EI-MS m/e (%): 171 (M+, 100), 170 ([M—H]+, 94).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 3 hours
  3. concentrationThe reaction mixture was then concentrated in vacuo
  4. additionOn addition of 50 ml water
  5. filtrationwas collected by filtration
  6. washwashed sequentially with water and ether

Sources & evidence

ORD record
ord-57cf3538cf62415b8cf3b5fbb05b5b99
Source dataset
uspto-grants-2003_07
Patent number
US06586441B2

Reaction notes

Loading…