Diethyl Ether → 4-(2-(Chloromethyl)pyrimidin-4-yl)morpholine hydrochloride

HRID 867882Notes

Reaction equation

HRID 867882 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[N:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:10]=[CH:9][N:8]=1.CCOCC>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:6][C:7]1[N:12]=[C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[CH:10]=[CH:9][N:8]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 24386Thionyl ChlorideHCID 14306153[4-(Morpholin-4-yl)pyrimidin-2-yl]methanol

Product 1

HCID 221669024-(2-(Chloromethyl)pyrimidin-4-yl)morpholine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (3.4 ml) was added dropwise to a stirred solution of 2-hydroxymethyl-4-morpholinopyrimidine in chloroform (30 ml) cooled in an ice bath. The mixture was allowed to warm to room temperature and left to stand for a further 1.5 hours. The solution was reduced to low volume, and ether added with stirring to give 2-chloromethyl-4-morpholinopyrimidine hydrochloride (3.8 g) as a crystalline solid, m.p. 214°-6°.

Workup

  1. temperaturecooled in an ice bath
  2. waitleft
  3. additionadded

Sources & evidence

ORD record
ord-1ad81b68dc804ddb87261471b6d43227
Source dataset
uspto-grants-1988_10
Patent number
US04777172

Reaction notes

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