Potassium Carbonate → HCID 86634076, compound

HRID 1041732Notes

Reaction equation

HRID 1041732 reaction equation
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([CH3:11])[C:9]=1[NH2:10])=[O:4].C(=O)([O-])[O-].[K+].[K+].[Cl:24][C:25]1[C:26](Cl)=[N:27][C:28]([Cl:31])=[N:29][CH:30]=1>CN(C=O)C.C(OCC)(=O)C>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[C:8]([CH3:11])[C:9]=1[NH:10][C:26]1[C:25]([Cl:24])=[CH:30][N:29]=[C:28]([Cl:31])[N:27]=1)=[O:4]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 2372592,4,5-TrichloropyrimidineHCID 2756498HCID 2756498, compound

Product 1

HCID 86634076HCID 86634076, compoundYield 2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 3-amino-4-methyl-5-phenyl-thiophene-2-carboxylic acid methyl ester (1.25 g, 5.06 mmol), potassium carbonate (0.7 g, 5.06 mmol) and trichloropyrimidine (2.78 g, 15.2 mmol) was heated at 50° C. in DMF (10 mL) for 16 hours. The mixture was diluted with ethyl acetate, washed with brine and water, and dried over sodium sulfate. Evaporation of solvent and column chromatography (hexane and ethyl acetate (9:1)) gave 39 mg of 3-(2,5-dichloro-pyrimidin-4-ylamino)-4-methyl-5-phenyl-thiophene-2-carboxylic acid methyl ester in 2% yield: 1H NMR (300 MHz, CDCl3) δ 8.58 (s, 1H), 7.5 (m, 5H), 3.82 (s, 3H), 2.37 (s, 3H); MS (m/e): 393.9 (M+1).

Workup

  1. washwashed with brine and water
  2. dry with materialdried over sodium sulfate
  3. customEvaporation of solvent and column chromatography (hexane and ethyl acetate (9:1))

Sources & evidence

ORD record
ord-f7ddc841edc84d28a7bf65099a48976a
Source dataset
uspto-grants-2013_10
Patent number
US08552186B2

Reaction notes

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