Trifluoroacetic acid → 2-(Trifluoromethyl)thieno[3,2-d]pyrimidin-4(3H)-one

HRID 41360

Reaction equation

HRID 41360 reaction equation
[NH2:1][C:2]1[CH:6]=[CH:5][S:4][C:3]=1[C:7]([O:9]C)=O.[F:11][C:12]([F:17])([F:16])[C:13](N)=[NH:14].FC(F)(F)C(O)=O>CCO>[F:11][C:12]([F:17])([F:16])[C:13]1[NH:14][C:7](=[O:9])[C:3]2[S:4][CH:5]=[CH:6][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 89652Methyl 3-amino-2-thiophenecarboxylateHCID 2776882Trifluoroacetamidine

Product 1

HCID 1356253762-(Trifluoromethyl)thieno[3,2-d]pyrimidin-4(3H)-oneYield 27.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

To a stirring solution of methyl 3-aminothiophene-2-carboxylate (45a, 1.57, 10.0 mmol) in EtOH (10 mL) was added trifluoroacetamidine (2.24 g, 2 eq) and trifluoroacetic acid (1.54 ml, 2 eq). The resulting mixture was heated to 150° C. for 1 hour in microwave reactor. The reaction mixture was cool and filtered to provide 2-(trifluoromethyl)thieno[3,2-d]pyrimidine-4(3H)-one 45b as a solid (0.61 g). 1H NMR (400 MHz, MeOD) δ ppm: 7.49 (d, J=5.29 Hz, 2H), 8.18 (d, J=5.29 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was cool
  2. filtrationfiltered

Sources & evidence

ORD record
ord-88166c9d0f1d4e5aa800b48d75bbf0f0
Source dataset
uspto-grants-2013_09
Patent number
US08530652B2

Linked notes

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