Dimethylformamide → Methyl 2-(4,6-dimethoxypyrimidin-2-yl)oxyhexanoate

HRID 1073029Notes

Reaction equation

HRID 1073029 reaction equation
[OH:1][C:2]1[N:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[N:3]=1.Br[CH:13]([CH2:18][CH2:19][CH2:20][CH3:21])[C:14]([O:16][CH3:17])=[O:15].CN(C)C=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:9][O:8][C:6]1[CH:5]=[C:4]([O:10][CH3:11])[N:3]=[C:2]([O:1][CH:13]([CH2:18][CH2:19][CH2:20][CH3:21])[C:14]([O:16][CH3:17])=[O:15])[N:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 95578Hexanoic acid, 2-bromo-, methyl esterHCID 178493557HCID 178493557, compound

Product 1

HCID 15070278Methyl 2-(4,6-dimethoxypyrimidin-2-yl)oxyhexanoateYield 73.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3.5 g of 2-hydroxy-4,6-dimethoxypyrimidine, 4.7 g of methyl 2-bromohexanoate, 50 ml of N,N-dimethylformamide and 3.3 g of anhydrous potassium carbonate were stirred at a temperature of from 85° to 90° C. for 3 hours. The reaction mixture was cooled to room temperature and then diluted with water. This aqueous mixture was extracted with ethyl ether. The ethyl ether extract was washed with water and dried. Then, ethyl ether was removed by distillation under reduced pressure to obtain a slightly yellow oily substance. The slightly yellow oily substance was purified by silica gel column chromatography (eluent: hexane/ethyl acetate =6/1) to obtain 4.7 g of the desired product.

Workup

  1. extractionThis aqueous mixture was extracted with ethyl ether
  2. extractionThe ethyl ether extract
  3. washwas washed with water
  4. customdried
  5. customThen, ethyl ether was removed by distillation under reduced pressure
  6. customto obtain a slightly yellow oily substance
  7. customThe slightly yellow oily substance was purified by silica gel column chromatography (eluent: hexane/ethyl acetate =6/1)

Sources & evidence

ORD record
ord-852c88e170454d11a6857fbf0d58e048
Source dataset
uspto-grants-1990_11
Patent number
US04968340

Reaction notes

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