Iodoethane → 6-chloro-1-ethyl-5-isopropyl-1H-pyrimidine-2,4-dione

HRID 2194761Notes

Reaction equation

HRID 2194761 reaction equation
[Cl:1][C:2]1[NH:7][C:6](=[O:8])[NH:5][C:4](=[O:9])[C:3]=1[CH:10]([CH3:12])[CH3:11].C(=O)([O-])[O-].[K+].[K+].I[CH2:20][CH3:21]>CN(C=O)C>[Cl:1][C:2]1[N:7]([CH2:20][CH3:21])[C:6](=[O:8])[NH:5][C:4](=[O:9])[C:3]=1[CH:10]([CH3:12])[CH3:11]

Participants

5

Reactant 3

HCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 111270436-Chloro-5-isopropylpyrimidine-2,4(1H,3H)-dione

Product 1

HCID 582035056-chloro-1-ethyl-5-isopropyl-1H-pyrimidine-2,4-dione

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

6-Chloro-5-isopropyl-1H-pyrimidine-2,4-dione (18.8 g, 100 mmol) was stirred with anhydrous powdered potassium carbonate (16.56 g, 120 mmol) in DMF (200 mL) at room temperature. After 40 min., iodoethane (8 mL, 100 mmol) was added and the mixture was stirred overnight. The mixture was evaporated in vacuo and the residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (from 1:4 to 1:2)) to give 13.8 (63%) of 6-chloro-1-ethyl-5-isopropyl-1H-pyrimidine-2,4-dione as a white solid. m.p. 160-161° C.; 1H-NMR (200 MHz, CDCl3) δ 1.28-1.35 (9H, m), 3.22 (1H, m), 4.15 (2H, q, J=7.2 Hz); m/z (EI) 216 (M+).

Workup

  1. customThe mixture was evaporated in vacuo
  2. customthe residue was purified by silica gel column chromatography (eluent, ethyl acetate:hexane (from 1:4 to 1:2))

Sources & evidence

ORD record
ord-9ba2e65bc98b4a4a88a1116858692dc2
Source dataset
uspto-grants-2012_12
Patent number
US08334295B2

Reaction notes

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