Dimethylformamide → 4,5-Dichloro-2-cyclopropyl-6-(diethoxymethyl)pyrimidine

HRID 907427Notes

Reaction equation

HRID 907427 reaction equation
P(Cl)(Cl)([Cl:3])=O.[Cl:6][C:7]1[C:8](=O)[N:9]=[C:10]([CH:20]2[CH2:22][CH2:21]2)[NH:11][C:12]=1[CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16].CN(C)C=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[Cl:3][C:8]1[C:7]([Cl:6])=[C:12]([CH:13]([O:17][CH2:18][CH3:19])[O:14][CH2:15][CH3:16])[N:11]=[C:10]([CH:20]2[CH2:22][CH2:21]2)[N:9]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 1784711825-chloro-2-cyclopropyl-6-(diethoxymethyl)-1H-pyrimidin-4-one2×

Product 1

HCID 866281754,5-Dichloro-2-cyclopropyl-6-(diethoxymethyl)pyrimidineYield 95%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

Phosphorus oxychloride (35.1 g, 0.229 mol) in toluene (93 mL) was added to 5-chloro-2-cyclopropyl-6-(diethoxymethyl)-4(1H)-pyrimidinone (i.e. the product of Example 4) (51.75 g, 0.190 mol) and N,N-dimethylformamide (34.7 g, 0.475 mol) in toluene (186 mL) at −5 to 0° C. The mixture was allowed to warm to room temperature over about 2 h. Then the mixture was added to aqueous sodium carbonate solution (saturated, 600 mL). The aqueous phase was further extracted with ethyl acetate (4×50 mL), and the organic extracts were combined, dried and evaporated to leave the product as an oil (52.9 g, 95% yield).

Workup

  1. extractionThe aqueous phase was further extracted with ethyl acetate (4×50 mL)
  2. customdried
  3. customevaporated

Sources & evidence

ORD record
ord-1b81cc64a8ee4b929c74a5c71d793267
Source dataset
uspto-grants-2011_09
Patent number
US08013155B2

Reaction notes

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