Water → HCID 10890607, compound

HRID 2299722Notes

Reaction equation

HRID 2299722 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-04e958f1b6fc4a20bc372c5866bb7d4b
Source dataset
uspto-grants-2002_12
Patent number
US06495581B1

Reaction notes

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