Water → HCID 10890607, compound

HRID 1070047Notes

Reaction equation

HRID 1070047 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-bexane 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-bexane

Sources & evidence

ORD record
ord-080288b80e60470eaf62911671af8a60
Source dataset
uspto-grants-2001_06
Patent number
US06251926B1

Reaction notes

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