Ethyl orthoformate → 6-(2,2,2-Trifluoroethyl)thieno[2,3-d]pyrimidin-4(1H)-one

HRID 1505641Notes

Reaction equation

HRID 1505641 reaction equation
[NH2:1][C:2]1[S:3][C:4]([CH2:10][C:11]([F:14])([F:13])[F:12])=[CH:5][C:6]=1[C:7]([NH2:9])=[O:8].[CH2:15](OC(OCC)OCC)C>C(O)(=O)C>[F:13][C:11]([F:12])([F:14])[CH2:10][C:4]1[S:3][C:2]2[N:1]=[CH:15][NH:9][C:7](=[O:8])[C:6]=2[CH:5]=1

Participants

4

Reactant 2

HCID 31214Ethyl orthoformateHCID 904044682-Amino-5-(2,2,2-trifluoroethyl)-thiophene-3-carboxamide

Product 1

HCID 904054626-(2,2,2-Trifluoroethyl)thieno[2,3-d]pyrimidin-4(1H)-one

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

8.4 g of 2-amino-5-(2,2,2-trifluoroethyl)thiophene-3-carboxamide was refluxed in a mixture of 28 mL of triethylorthoformate and 20 mL of acetic acid for 4 hs. Solvents were removed under reduced pressure and the residue was triturated hexane-ethyl acetate mixture (1:1). The solid was filtered off to afford 5.7 g of 6-(2,2,2-trifluoroethyl)thieno[2,3-d]pyrimidin-4(3H)-one. 1H NMR MeOH-d4 (300 MHz): 12.6 (br, 1H), 8.14 (s, 1H), 7.42 (s, 1H), 4.07 (q, 2H, J 11.0 Hz). 13C NMR MeOH-d4 (75 MHz): 164.5, 157.01, 146.1, 128.4, 124.6, 123.5, 33.6 (q, J31.5 Hz).

Workup

  1. customSolvents were removed under reduced pressure
  2. customthe residue was triturated hexane-ethyl acetate mixture (1:1)
  3. filtrationThe solid was filtered off

Sources & evidence

ORD record
ord-969fbeec39be411db4f78a22932365f4
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Reaction notes

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