Trifluoroacetic acid → HCID 178429622, compound

HRID 711662Notes

Reaction equation

HRID 711662 reaction equation
[NH2:1][C:2]1[C:3]2[C:11]([CH3:12])=[C:10]([C:13]([O:15]C(C)(C)C)=[O:14])[S:9][C:4]=2[NH:5][C:6](=[O:8])[N:7]=1.FC(F)(F)C(O)=O>C(Cl)Cl>[NH2:1][C:2]1[C:3]2[C:11]([CH3:12])=[C:10]([C:13]([OH:15])=[O:14])[S:9][C:4]=2[NH:5][C:6](=[O:8])[N:7]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 178429605HCID 178429605, compound

Product 1

HCID 178429622HCID 178429622, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of tert-butyl 4-amino-5-methyl-2-oxo-1,2-dihydrothieno[2,3-d]pyrimidine-6-carboxylate (example 64a) (10.7 g, 38.03 mmol) in CH2Cl2 (25 mL), was added trifluoroacetic acid (25 mL, 324.5 mmol). The reaction mixture was stirred at rt overnight. The precipitated solid was collected by filtration, and washed with CH2Cl2 to yield 4-Amino-5-methyl-2-oxo-1,2-dihydrothieno[2,3-d]pyrimidine-6-carboxylic acid (6.98 g, 82%) as a light brown solid. 1H NMR (400 MHz, DMSO-d6) δ 2.78 (s, 3H). MS 226.0 (MH+).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. washwashed with CH2Cl2

Sources & evidence

ORD record
ord-935f6e534a1e4d22afea5d63575d8f48
Source dataset
uspto-grants-2015_11
Patent number
US09181276B2

Reaction notes

Loading…