Sodium Hydroxide → 5,7-Dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid

HRID 530962Notes

Reaction equation

CC(=O)CC(=O)C.NC1C(C(OCC)=O)=CNN=1.[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[N:23]2[N:27]=[CH:28][C:29]([C:30]([O:32]CC)=[O:31])=[C:22]2[N:21]=1.[OH-].[Na+]>CO.C(OCC)C.C(O)(=O)C>[CH3:19][C:20]1[CH:25]=[C:24]([CH3:26])[N:23]2[N:27]=[CH:28][C:29]([C:30]([OH:32])=[O:31])=[C:22]2[N:21]=1

Participants

Conditions

Temperature: 75 °C

Procedure

Pentane-2,4-dione (1.46 ml, 14.2 mmol), ethyl 3-amino-1H-pyrazole-4-carboxylate (2.00 g, 12.9 mmol) were heated in a sealed tube with acetic acid (10 ml) at 110° C. overnight. The reaction reached completion by LCMS (LC-MS: rt (min)=3.08). The acetic acid was removed by blowing air with the flask being heated to 75° C. The crude residue of ethyl 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylate (assumed to be 12.89 mmol) was suspended in MeOH (15 ml) and treated with 7.2 M sodium hydroxide (5.37 ml, 38.7 mmol). The mixture was heated to 80° C. (at this temperature the solid dissolved) and then stirred for 3 h. The reaction was cooled and the neutralized to pH 6-7. The slurry was filtered via a Büchner funnel under house vacuum, the solid residue was washed with water and then diethyl ether to obtain 5,7-dimethylpyrazolo[1,5-a]pyrimidine-3-carboxylic acid (1.4 g, 7.3 mmol, 57% yield). LC-MS: rt (min)=2.61. 1H NMR (400 MHz, DMSO-d6) δ ppm 2.57 (s, 3H), 2.71 (s, 3H), 7.10 (s, 1H), 8.50 (s, 1H).

Workup

customby LCMS (LC-MS: rt (min)=3.08)
customThe acetic acid was removed
temperatureThe mixture was heated to 80° C. (at this temperature the solid
dissolutiondissolved) and
temperatureThe reaction was cooled
filtrationThe slurry was filtered via a Büchner funnel under house vacuum
washthe solid residue was washed with water

Sources & evidence

ORD record: ord-a4356d078839453f8a7c413c287052d2
Source dataset: uspto-grants-2016_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09353117B2

Reaction notes

Loading…