Hydrochloric Acid → 4,5,6,7-Tetrahydro-7,7-dimethyl-5-phenylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 63759Notes

Reaction equation

[CH3:1][C:2]1([CH3:22])[N:7]2[N:8]=[CH:9][C:10]([C:11]([O:13]CC)=[O:12])=[C:6]2[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3]1.[OH-].[K+].O.Cl>CCO>[CH3:1][C:2]1([CH3:22])[N:7]2[N:8]=[CH:9][C:10]([C:11]([OH:13])=[O:12])=[C:6]2[NH:5][CH:4]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH2:3]1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 1 (0.73 g) obtained in Example 1009, KOH (0.41 g), H2O (20 ml) and EtOH (20 mL) was stirred at 90° C. for 12 h, acidified with 1N HCl, and extracted with AcOEt. The extract was washed with brine, dried over MgSO4, and concentrated in vacuo to give 0.55 g (83% yield) of the title compound as colorless prisms ([α]D20° C.=−85.33, in CHCl3, C=0.46). mp 205-206° C., 1H NMR (CDCl3, 300 MHz): 1.59 (3H, s), 1.66 (3H, s), 2.05-2.15 (2H, m), 4.64 (1H, dd, J=9.6, 5.4 Hz), 6.04 (1H, s), 7.30-7.41 (5H, m), 7.73 (1H, s).

Workup

extractionextracted with AcOEt
washThe extract was washed with brine
dry with materialdried over MgSO4
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-fcf66a74307942038e9f069bc28b8e7e
Source dataset: uspto-grants-2016_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09447100B2

Reaction notes

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