Triethylamine → 5-Chloro-1-{[(2-methylphenyl)methoxy]methyl}pyrimidin-2(1H)-one

HRID 1719239Notes

Reaction equation

HRID 1719239 reaction equation
[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][O:5][CH2:6]Cl.Cl.[Cl:13][C:14]1[CH:15]=[N:16][C:17](=[O:20])[NH:18][CH:19]=1.C(N(CC)CC)C>ClCCl>[CH3:1][C:2]1[CH:11]=[CH:10][CH:9]=[CH:8][C:3]=1[CH2:4][O:5][CH2:6][N:18]1[CH:19]=[C:14]([Cl:13])[CH:15]=[N:16][C:17]1=[O:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 126485235-Chloropyrimidin-2-ol hydrochlorideHCID 131405831-((Chloromethoxy)methyl)-2-methylbenzene

Product 1

HCID 156504925-Chloro-1-{[(2-methylphenyl)methoxy]methyl}pyrimidin-2(1H)-oneYield 96.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of chloromethyl 2-methylbenzyl ether (see Preparation 3a and 3b) (10 mmol) in dichloromethane (20 ml) was added dropwise with stirring to a solution of 5-chloropyrimidin-2-one hydrochloride (10 mmol) and triethylamine (20 mmol) in dichloromethane (80 ml). The reaction mixture was stirred for 2 hours at room temperature. It was then washed with water and the dried (MgSO4) solution evaporated to yield a crude mixture (2.55 g, 96%) which was purified by trituration with ether. The yield of the title compound was 1.33 g (50%), m.p. 88° C. 1H NMR (CDCl3): δ2.26 (Me), 4.63 (CH2 -Ph), 5.30 (CH2O), 7.00 (Ph), 7.60 and 8.37 (H-4, H-6, J 4 Hz). IR(KBr): 1660 cm-1 (CO).

Workup

  1. washIt was then washed with water
  2. dry with materialthe dried (MgSO4) solution
  3. customevaporated

Sources & evidence

ORD record
ord-82f12a538f0249c5b446c341768da59a
Source dataset
uspto-grants-1985_09
Patent number
US04539324

Reaction notes

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