Water → HCID 70347348, compound

HRID 1417163Notes

Reaction equation

HRID 1417163 reaction equation
[CH3:1]C(C)([O-])C.[K+].[Cl:7][C:8]1[S:12][C:11]([C:13]2[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:17]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=1.[CH3:30][O:31][C:32]1[CH:37]=[C:36]([O:38][CH3:39])[N:35]=[C:34](S(C)(=O)=O)N=1.O>CN(C)C=O>[Cl:7][C:8]1[S:12][C:11]([C:13]2[C:18]([C:19]([O:21][CH2:22][CH3:23])=[O:20])=[C:17]([CH:24]([C:34]3[CH:1]=[C:32]([O:31][CH3:30])[CH:37]=[C:36]([O:38][CH3:39])[N:35]=3)[C:25]([O:27][CH2:28][CH3:29])=[O:26])[N:16]=[CH:15][CH:14]=2)=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 962WaterHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 23665647Potassium tert-butoxideHCID 53843286HCID 53843286, compound

Product 1

HCID 70347348HCID 70347348, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

Next, 2.9 g of potassium t-butoxide was added to 50 ml of N,N-dimethylformamide. To the resulting mixture, 8.9 g of ethyl 4-(5-chlorothiophen-2-yl)-2-(α-ethoxycarbonylmethyl)nicotinate dissolved in N,N-dimethylformamide was added dropwise at -10° C., and the resulting reaction solution was stirred at room temperature for 1 hour. 5.6 g of 4,6-dimethoxy-2-methylsulfonylpyrimidine was added thereto, and the reaction solution was stirred at a temperature of from 60° C. to 80° C. for 8 hours. After completion of the reaction, the reaction solution was poured into water and brought to pH 4-5 and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate. The ethyl acetate was distilled off, and the residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1) to obtain 2.7 g (yield 23%) of the desired compound. m.p.: 127°-132° C.

Workup

  1. additionwas added dropwise at -10° C.
  2. customthe resulting reaction solution
  3. stirringthe reaction solution was stirred at a temperature of from 60° C. to 80° C. for 8 hours
  4. customAfter completion of the reaction
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous magnesium sulfate
  8. distillationThe ethyl acetate was distilled off
  9. customthe residue was purified by silica gel column chromatography (hexane:ethyl acetate=5:1)

Sources & evidence

ORD record
ord-8e200ee970f0427396b9e6b1cddd01b2
Source dataset
uspto-grants-1999_03
Patent number
US05877120

Reaction notes

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