Hydrazine hydrate (1:1) → 5-Aminomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine

HRID 4690Notes

Reaction equation

HRID 4690 reaction equation
[CH3:1][C:2]1[N:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)[C:3]=1[CH2:23][N:24]1C(=O)C2=CC=CC=C2C1=O.O.NN>C(O)C>[NH2:24][CH2:23][C:3]1[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[C:16]([N+:20]([O-:22])=[O:21])[CH:15]=2)=[N:5][C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)=[N:7][C:2]=1[CH3:1]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 201514046-Methyl-4-(3-nitrophenyl)-5-phthalimidomethyl-2-phenylpyrimidine

Product 1

HCID 201514135-Aminomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidineYield 22.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 6-methyl-4-(3-nitrophenyl)-5-phthalimidomethyl-2-phenylpyrimidine (6.9 g) and hydrazine monohydrate (0.8 g) in ethanol (140 ml) was refluxed for 6 hours. After filtering off the insolubles, the filtrate was poured into a suspension of chloroform (200 ml) and water (300 ml) under stirring. The organic layer was separated, washed with aqueous sodium chloride and dried over magnesium sulfate. The solvent was evaporated in vacuo and the resulting crystals were recrystallized from ethanol to give 5-aminomethyl-6-methyl-4-(3-nitrophenyl)-2-phenylpyrimidine (1.12 g).

Workup

  1. temperaturewas refluxed for 6 hours
  2. filtrationAfter filtering off the insolubles
  3. additionthe filtrate was poured into a suspension of chloroform (200 ml) and water (300 ml)
  4. customThe organic layer was separated
  5. washwashed with aqueous sodium chloride
  6. dry with materialdried over magnesium sulfate
  7. customThe solvent was evaporated in vacuo
  8. customthe resulting crystals were recrystallized from ethanol

Sources & evidence

ORD record
ord-875c847cb5274fd89a51931bb3c68eed
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Reaction notes

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