Sodium borohydride → HCID 178433453, compound

HRID 1463061Notes

Reaction equation

HRID 1463061 reaction equation
[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][C:9](OCC)=[O:10])[N:5]=[C:4]([CH3:14])[N:3]=1.[BH4-].[Na+]>C(O)(C)C>[OH:1][C:2]1[CH:7]=[C:6]([CH2:8][CH2:9][OH:10])[N:5]=[C:4]([CH3:14])[N:3]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 178470724HCID 178470724, compound

Product 1

HCID 178433453HCID 178433453, compoundYield 50.2%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

A solution of ethyl (4-hydroxy-2-methylpyrimid-6-yl)acetate (0.38 g.) in isopropanol (10 ml.) was heated under reflux and treated with sodium borohydride (0.2 g.). The mixture was heated under reflux for 4 hours with the addition of two further portions (0.1 g.) of sodium borohydride after 2 and 3 hours. The mixture was evaporated to dryness and the residue was partitioned between water and ether. The aqueous phase was acidifed with HOAc and then extracted with EtOAc in a continuous extractor for 24 hours. The extract was dried and then evaporated to dryness to give 4-hydroxy-6-(2-hydroxyethyl)-2-methylpyrimidine (0.15 g.) which was used without further purification.

Workup

  1. temperatureunder reflux
  2. temperatureThe mixture was heated
  3. customThe mixture was evaporated to dryness
  4. customthe residue was partitioned between water and ether
  5. extractionextracted with EtOAc in a continuous extractor for 24 hours
  6. customThe extract was dried
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-a1571b8f536543fda2ecdda17b6f1c01
Source dataset
uspto-grants-1984_07
Patent number
US04463005

Reaction notes

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