Acetic Acid → HCID 14722193, compound

HRID 2352184Notes

Reaction equation

HRID 2352184 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:13][C:14]3[CH:15]=[C:16](C(=O)C)[CH:17]=[CH:18][CH:19]=3)[N:8]=2)[CH:2]=1.[BH4-].[Na+].[C:25](O)(=[O:27])[CH3:26]>C(O)C>[CH3:26][CH:25]([C:17]1[CH:18]=[CH:19][C:14]([NH:13][C:9]2[N:8]=[C:7]([C:3]3[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=3)[CH:12]=[CH:11][N:10]=2)=[CH:15][CH:16]=1)[OH:27]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 4311764Sodium borohydride2×HCID 14347154HCID 14347154, compound

Product 1

HCID 14722193HCID 14722193, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A 1.45 g portion of 1-[3-[[4-(3-pyridinyl)-2-pyrimidinyl]amino]phenyl]ethanone was dissolved with stirring in 220 ml of ethanol. A 125 mg portion of sodium borohydride was added and stirring continued for 3 hours. A 63 mg portion of sodium borohydride was added and stirring continued overnight. A 2 ml portion of glacial acetic acid was added and the mixture evaporated. The solid was triturated with water, dried and recrystallized from 30 ml of ethanol giving 710 mg of the desired product, mp 145°-147° C.

Workup

  1. stirringstirring continued overnight
  2. customthe mixture evaporated
  3. customThe solid was triturated with water
  4. customdried
  5. customrecrystallized from 30 ml of ethanol giving 710 mg of the desired product, mp 145°-147° C.

Sources & evidence

ORD record
ord-05286753fe8a4c3db085f6b624ace7a4
Source dataset
uspto-grants-1989_10
Patent number
US04876252

Reaction notes

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