Hydrochloric Acid → 4-[6-(Difluoromethoxy)pyrazolo[1,5-a]pyrimidin-3-yl]-5-methylthiophene-2-carboxylic acid

HRID 1842607Notes

Reaction equation

C[O:2][C:3]([C:5]1[S:6][C:7]([CH3:23])=[C:8]([C:10]2[CH:11]=[N:12][N:13]3[CH:18]=[C:17]([O:19][CH:20]([F:22])[F:21])[CH:16]=[N:15][C:14]=23)[CH:9]=1)=[O:4].[OH-].[K+].CO.Cl>C1COCC1>[F:22][CH:20]([F:21])[O:19][C:17]1[CH:16]=[N:15][C:14]2[N:13]([N:12]=[CH:11][C:10]=2[C:8]2[CH:9]=[C:5]([C:3]([OH:4])=[O:2])[S:6][C:7]=2[CH3:23])[CH:18]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Methyl-4-[6-(difluoromethoxy)pyrazolo[1,5-a]pyrimidin-3-yl]-5-methylthiophene-2-carboxylate (0.916 g, 2.70 mmol) was dissolved in THF (4 mL). 1 M KOH in MeOH (12.0 mL, 12.0 mmol) was added and the reaction heated to 40° C. for 16 h. After the hydrolysis was complete, treated with 1N HCl and the resulting solids were filtered, washed with water and dried to afford the title compound (0.568 g, 1.75 mmol). LRMS (APCI) calc'd for (C13H9F2N3O3S) [M+H]+, 326.0; found 326.0.

Workup

filtrationthe resulting solids were filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-1e437e41b5dd443d90caf748b8be3afa
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08946237B2

Reaction notes

Loading…