Water → 6-(2-Dimethylaminoethyl)-5-(1-hydroxyethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine

HRID 4691Notes

Reaction equation

HRID 4691 reaction equation
[C:1]([C:4]1[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)=[N:6][C:7]([C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[N:8][C:9]=1[CH2:10][CH2:11][N:12]([CH3:14])[CH3:13])(=[O:3])[CH3:2].[BH4-].[Na+].O.C(Cl)(Cl)Cl>CO>[CH3:14][N:12]([CH3:13])[CH2:11][CH2:10][C:9]1[N:8]=[C:7]([C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][CH:20]=2)[N:6]=[C:5]([C:21]2[CH:26]=[CH:25][CH:24]=[C:23]([N+:27]([O-:29])=[O:28])[CH:22]=2)[C:4]=1[CH:1]([OH:3])[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 6212ChloroformHCID 4311764Sodium borohydrideHCID 10452990HCID 10452990, compound

Product 1

HCID 201514076-(2-Dimethylaminoethyl)-5-(1-hydroxyethyl)-4-(3-nitrophenyl)-2-phenylpyrimidineYield 19.9%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A mixture of 5-acetyl-6-(2-dimethylaminoethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (1 g) and sodium borohydride (0.1 g) in methanol (40 ml) was stirred for 1 hour. The reaction mixture was poured into a mixture of water and chloroform and adjusted the pH to 9. The extract was dried over magnesium sulfate and evaporated in vacuo. The residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (20:1). The fractions containing the desired product were combined and concentrated in vacuo. The residue was recrystallized from diethyl ether to afford 6-(2-dimethylaminoethyl)-5-(1-hydroxyethyl)-4-(3-nitrophenyl)-2-phenylpyrimidine (0.2 g).

Workup

  1. dry with materialThe extract was dried over magnesium sulfate
  2. customevaporated in vacuo
  3. customThe residue was chromatographed on silica gel eluting with a mixture of chloroform and methanol (20:1)
  4. additionThe fractions containing the desired product
  5. concentrationconcentrated in vacuo
  6. customThe residue was recrystallized from diethyl ether

Sources & evidence

ORD record
ord-39086401e8144ed4a96b7c62ec12a729
Source dataset
uspto-grants-1988_02
Patent number
US04727073

Reaction notes

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