Sodium borohydride → HCID 14856037, compound

HRID 1032698Notes

Reaction equation

HRID 1032698 reaction equation
[BH4-].[Na+].[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:17]=[CH:18][C:19]3[CH2:24][C:23](=[O:25])[N:22]([CH3:26])[C:20]=3[N:21]=2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1>C(O)C>[CH2:3]([N:10]1[CH2:15][CH2:14][N:13]([C:16]2[N:21]=[C:20]([NH:22][CH3:26])[C:19]([CH2:24][CH2:23][OH:25])=[CH:18][N:17]=2)[CH2:12][CH2:11]1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 13784152HCID 13784152, compound

Product 1

HCID 14856037HCID 14856037, compoundYield 30%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (2.24 g) was added to 8.0 g of 2-(4-benzylpiperazino)-5,6-dihydro-7-methyl-6-oxo-(7H)pyrrolo[2,3-d]pyrimidine (produced in accordance with Referential Example 54 of Japanese Laid-Open Patent Publication No. 140568/1986) and 400 ml of ethanol, and the mixture was heated under reflux for 1.5 hours. The reaction mixture was concentrated. The residue was mixed with water and extracted with ethyl acetate. The organic layer was dried over anhydrous sodium sulfate, and the solvent was evaporated. The residue was purified by silica gel column chromatography (methanol:chloroform=1:10), and recrystallized from toluene to give 2.4 g (yield 30%) of 2-(4-benzylpiperazino)-5-(2-hydroxyethyl)-4-methylaminopyrimidine as colorless crystals.

Workup

  1. customproduced in accordance with Referential Example 54 of Japanese Laid-Open Patent Publication No
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe reaction mixture was concentrated
  4. additionThe residue was mixed with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  7. customthe solvent was evaporated
  8. customThe residue was purified by silica gel column chromatography (methanol:chloroform=1:10)
  9. customrecrystallized from toluene

Sources & evidence

ORD record
ord-f0ba549067474c01bad91cb60cf20712
Source dataset
uspto-grants-1990_09
Patent number
US04959368

Reaction notes

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