Hydrazine, dihydrochloride → HCID 71268922, compound

HRID 1049962Notes

Reaction equation

HRID 1049962 reaction equation
[CH:1]([C:3]1[C:8]([C:9]([O:11]CC)=O)=[C:7]([S:14][CH3:15])[N:6]=[C:5]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[N:4]=1)=O.Cl.Cl.[NH2:24][NH2:25]>C(O)C>[CH3:15][S:14][C:7]1[C:8]2[C:9](=[O:11])[NH:25][N:24]=[CH:1][C:3]=2[N:4]=[C:5]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[N:6]=1

Participants

4

Reactant 2

HCID 17548Hydrazine, dihydrochlorideHCID 866770205-Pyrimidinecarboxylic acid, 4-formyl-6-(methylthio)-2-phenyl-, ethyl ester

Product 1

HCID 71268922HCID 71268922, compoundYield 97.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of ethyl 4-formyl-6-(methylthio)-2-phenylpyrimidine-5-carboxylate (600 mg, 1.98 mmol) in ethanol (15 mL) was added hydrazine dihydrochloride (0.2 g, 1.98 mmol) and the mixture refluxed for 1 hour. The precipitated solid was filtered and dried in vacuum. The desired product (520 mg) was obtained by column chromatography over silica gel using methanol/dichloromethane as eluent. 1H-NMR (400 Hz, DMSO-d6): δ 13.19 (s, 1H), 8.54 (d, J=8.0 Hz, 2H), 8.36 (s, 1H), 7.64-7.58 (m, 3H), 2.67 (s, 3H); MS m/z 271.1 (M+1).

Workup

  1. temperaturethe mixture refluxed for 1 hour
  2. filtrationThe precipitated solid was filtered
  3. customdried in vacuum

Sources & evidence

ORD record
ord-a8c721d3d257453e9785c23f0ad14f40
Source dataset
uspto-grants-2016_07
Patent number
US09382277B2

Reaction notes

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