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

HRID 620159Notes

Reaction equation

HRID 620159 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 67.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of boron tribromide (9.02 ml) in dichloromethane (100 ml) was added dropwise to a stirred solution of 2-methoxymethyl-4-morpholinopyrimidine (4.99 g) in dichloromethane (50 ml) at -25° under nitrogen. After 15 minutes the mixture was allowed to warm to 0°-5°, and left to stand for 2 hours at this temperature. After pouring onto ice, the pH was raised to 14 (NaOH), and the organic phase separated off. The aqueous phase was further extracted with chloroform, and the combined extracts dried (K2CO3) and stripped. The residue was triturated with ether to give 2-hydroxymethyl-4-morpholinopyrimidine (3.16 g) as a crystalline solid, m.p. 76°-8°.

Workup

  1. temperatureto warm to 0°-5°
  2. waitleft
  3. waitto stand for 2 hours at this temperature
  4. additionAfter pouring onto ice
  5. customthe organic phase separated off
  6. extractionThe aqueous phase was further extracted with chloroform
  7. dry with materialthe combined extracts dried (K2CO3)
  8. customThe residue was triturated with ether

Sources & evidence

ORD record
ord-2fae56e4f4214b9ea5b11a2d9788bf24
Source dataset
uspto-grants-1989_04
Patent number
US04820708

Reaction notes

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