Sodium Hydroxide → [4-(Morpholin-4-yl)pyrimidin-2-yl]methanol

HRID 1031879Notes

Reaction equation

HRID 1031879 reaction equation
B(Br)(Br)Br.C[O:6][CH2:7][C:8]1[N:13]=[C:12]([N:14]2[CH2:19][CH2:18][O:17][CH2:16][CH2:15]2)[CH:11]=[CH:10][N:9]=1.[OH-].[Na+]>ClCCl>[OH:6][CH2:7][C:8]1[N:13]=[C:12]([N:14]2[CH2:15][CH2:16][O:17][CH2:18][CH2:19]2)[CH:11]=[CH:10][N:9]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 25134Boron tribromideHCID 14421320HCID 14421320, compound

Product 1

HCID 14306153[4-(Morpholin-4-yl)pyrimidin-2-yl]methanolYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 24 ml of boron tribromide in 100 ml of dichloromethane was added dropwise, at -25° C. under a nitrogen atmosphere, to a solution of 13 g of 2-methoxymethyl-4-morpholinopyrimidine in 100 ml of dichloromethane. After 30 minutes at -25° C., the solution was left to stand at 0° C. for a further 2 hours and then poured onto ice. The solution was made alkaline with sodium hydroxide solution and was extracted with dichloromethane. After drying (Na2SO4) and concentration, diethyl ether was added, and 5.5 g of 2-hydroxymethyl-4-morpholinopyrimidine were obtained as a solid (melting point 76°-77° C.).

Workup

  1. waitthe solution was left
  2. waitto stand at 0° C. for a further 2 hours
  3. additionpoured onto ice
  4. extractionwas extracted with dichloromethane
  5. customAfter drying
  6. concentration(Na2SO4) and concentration, diethyl ether
  7. additionwas added

Sources & evidence

ORD record
ord-654675e9e4824075b0c89355c1f910c6
Source dataset
uspto-grants-1990_09
Patent number
US04956366

Reaction notes

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