3-(Trifluoromethyl)benzoyl chloride → (E)-N-(3-(2-(4-aminothieno[3,2-d]pyrimidine-7-yl)vinyl)-4-methylphenyl)-3-(trifluoromethyl)benzamide

HRID 1464983Notes

Reaction equation

HRID 1464983 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([CH3:20])=[C:6]([CH:19]=1)/[CH:7]=[CH:8]/[C:9]1[C:13]2[N:14]=[CH:15][N:16]=[C:17]([NH2:18])[C:12]=2[S:11][CH:10]=1.[F:21][C:22]([F:33])([F:32])[C:23]1[CH:24]=[C:25]([CH:29]=[CH:30][CH:31]=1)[C:26](Cl)=[O:27]>C1COCC1.C(OCC)(=O)C>[NH2:18][C:17]1[C:12]2[S:11][CH:10]=[C:9](/[CH:8]=[CH:7]/[C:6]3[CH:19]=[C:2]([NH:1][C:26](=[O:27])[C:25]4[CH:29]=[CH:30][CH:31]=[C:23]([C:22]([F:21])([F:32])[F:33])[CH:24]=4)[CH:3]=[CH:4][C:5]=3[CH3:20])[C:13]=2[N:14]=[CH:15][N:16]=1

Participants

5

Reactant 2

HCID 752573-(Trifluoromethyl)benzoyl chlorideHCID 67359028(E)-7-(5-amino-2-methylstyryl)thieno[3,2-d]pyrimidine-4-amine

Product 1

HCID 53345325(E)-N-(3-(2-(4-aminothieno[3,2-d]pyrimidine-7-yl)vinyl)-4-methylphenyl)-3-(trifluoromethyl)benzamideYield 86%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

(E)-7-(5-amino-2-methylstyryl)thieno[3,2-d]pyrimidine-4-amine (100 mg, 0.354 mmol) was dissolved in anhydrous THF, TEA (0.1 mL, 0.709 mmol) and 3-(trifluoromethyl)benzoyl chloride (81 mg, 0.390 mmol) were added thereto at room temperature and stirred for 4 hours. The reaction mixture was diluted with ethyl acetate and washed with brine. The organic layer was dried with MgSO4, filtered and concentrated. The resulting mixture was purified by silica gel chromatography to obtain the title compound (138 mg, 86% yield) (see Table 1).

Workup

  1. washwashed with brine
  2. dry with materialThe organic layer was dried with MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe resulting mixture was purified by silica gel chromatography

Sources & evidence

ORD record
ord-9ea71de677a248328c09c429bab04232
Source dataset
uspto-grants-2015_04
Patent number
US08999973B2

Reaction notes

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