Sodium borohydride → HCID 20183353, compound

HRID 255716Notes

Reaction equation

HRID 255716 reaction equation
[C:1]([C:4]1[C:5]([C:17]2[CH:22]=[CH:21][C:20]([N+:23]([O-:25])=[O:24])=[CH:19][CH:18]=2)=[N:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[N:8][C:9]=1[CH3:10])(=[O:3])[CH3:2].[BH4-].[Na+]>CO.O1CCCC1>[OH:3][CH:1]([C:4]1[C:5]([C:17]2[CH:18]=[CH:19][C:20]([N+:23]([O-:25])=[O:24])=[CH:21][CH:22]=2)=[N:6][C:7]([C:11]2[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=2)=[N:8][C:9]=1[CH3:10])[CH3:2]

Participants

5

Reactant 2

HCID 4311764Sodium borohydrideHCID 20183307HCID 20183307, compound

Product 1

HCID 20183353HCID 20183353, compoundYield 19.9%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

The mixture of 5-acetyl-6-methyl-4-(4-nitrophenyl)-2-phenyl-pyrimidine (1.5 g) and sodium borohydride (170 mg) in methanol (15 ml) and tetrahydrofuran (20 ml) was stirred for 2 hours at 5°-7° C. with ice cooling. The mixture was extracted with chloroform (100 ml) and 10% aqueous hydrochloric acid (50 ml). The separated organic layer was washed successively with saturated sodium hydrogen carbonate, saturated aqueous sodium chloride, dried over magnesium sulfate and evaporated in vacuo. The residue is recrystallized from ether to give 5-(1-hydroxyethyl)-6-methyl-4-(4-nitrophenyl)-2-phenylpyrimidine (0.3 g).

Workup

  1. extractionThe mixture was extracted with chloroform (100 ml) and 10% aqueous hydrochloric acid (50 ml)
  2. washThe separated organic layer was washed successively with saturated sodium hydrogen carbonate, saturated aqueous sodium chloride
  3. dry with materialdried over magnesium sulfate
  4. customevaporated in vacuo
  5. customThe residue is recrystallized from ether

Sources & evidence

ORD record
ord-927a1d60415d4433adea9e5027342977
Source dataset
uspto-grants-1987_10
Patent number
US04698340

Reaction notes

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