Chloromethyl Methyl Ether → 6-chloro-1-ethyl-5-isopropyl-3-methoxymethyl-1H-pyrimidine-2,4-dione

HRID 2194762Notes

Reaction equation

HRID 2194762 reaction equation
[Cl:1][C:2]1[N:7]([CH2:8][CH3:9])[C:6](=[O:10])[NH:5][C:4](=[O:11])[C:3]=1[CH:12]([CH3:14])[CH3:13].[H-].[Na+].[CH3:17][O:18][CH2:19]Cl>CN(C=O)C>[Cl:1][C:2]1[N:7]([CH2:8][CH3:9])[C:6](=[O:10])[N:5]([CH2:17][O:18][CH3:19])[C:4](=[O:11])[C:3]=1[CH:12]([CH3:13])[CH3:14]

Participants

5

Reactant 3

HCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 582035056-chloro-1-ethyl-5-isopropyl-1H-pyrimidine-2,4-dione

Product 1

HCID 582035516-chloro-1-ethyl-5-isopropyl-3-methoxymethyl-1H-pyrimidine-2,4-dioneYield 91.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a stirred solution of 6-chloro-1-ethyl-5-isopropyl-1H-pyrimidine-2,4-dione (11.5 g, 53 mmol) in DMF (100 mL) in a water bath, was added 60% NaH (3.18 g, 79.6 mmol). After stirring for 40 min., technical grade chloromethyl methyl ether (7.6 mL, 80 mmol) was added and the mixture was stirred at room temperature overnight. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:5)) to give 12.6 g (91%) of 6-chloro-1-ethyl-5-isopropyl-3-methoxymethyl-1H-pyrimidine-2,4-dione as a colorless oil. H-NMR (200 MHz, CDCl3) δ 1.26-1.34 (9H, m), 3.24 (1H, m), 3.44 (3H, s), 4.16 (2H, q, J=7.0 Hz), 5.35 (2H, s); m/z (EI) 260 (M+).

Workup

  1. stirringthe mixture was stirred at room temperature overnight
  2. customThe mixture was evaporated in vacuo
  3. customthe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (1:5))

Sources & evidence

ORD record
ord-2fd2aa543e2d46fc8c1e2fdfb56c9f86
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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