Water → HCID 10890607, compound

HRID 584363Notes

Reaction equation

HRID 584363 reaction equation
[CH3:1][N:2]([C:14]1[N:19]=[CH:18][CH:17]=[CH:16][N:15]=1)[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH:10]=[O:11])=[CH:8][CH:7]=1.O1CCCC1.[BH4-].[Na+].O>CO>[CH3:1][N:2]([C:14]1[N:15]=[CH:16][CH:17]=[CH:18][N:19]=1)[CH2:3][CH2:4][O:5][C:6]1[CH:13]=[CH:12][C:9]([CH2:10][OH:11])=[CH:8][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8028TetrahydrofuranHCID 4311764Sodium borohydrideHCID 100380894-[2-(N-Methyl-N-(2-pyrimidinyl)amino)ethoxy]-benzaldehyde

Product 1

HCID 10890607HCID 10890607, compoundYield 91.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-[2-(methyl-2-pyrimidylamino)ethoxy]benzaldehyde (16.6 g) in methanol (40 ml)-tetrahydrofuran (40 ml) was added sodium borohydride (1.22 g) in portions at 0° C. After stirring for 1 hour, water was added to the reaction mixture and extracted with ethyl acetate. The ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride, dried (MgSO4) and concentrated. The residual crystals were recrystallized from ethyl acetate-hexane to obtain 4-[2-(methyl-2-pyrimidylamino)ethoxy]benzylalcohol (15.3 g, yield 91%) as colorless crystals. m.p. 73-74° C.

Workup

  1. extractionextracted with ethyl acetate
  2. washThe ethyl acetate layer was washed with an aqueous saturated solution of sodium chloride
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe residual crystals were recrystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-478ae5fc4a0e49b4b8a973ee820864e7
Source dataset
uspto-grants-2005_08
Patent number
US06924300B2

Reaction notes

Loading…