Water → 4-[2-(4-Fluorophenyl)pyrazolo[1,5-a]pyridin-3-yl]-2-pyrimidinamine

HRID 1374717Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]([C:17](=O)[CH:18]=[CH:19]N(C)C)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:4][CH:3]=1.Cl.[NH2:25][C:26]([NH2:28])=[NH2+:27].C([O-])([O-])=O.[K+].[K+].O>CN(C)C=O>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:16]([C:17]3[CH:18]=[CH:19][N:25]=[C:26]([NH2:28])[N:27]=3)=[C:11]3[CH:12]=[CH:13][CH:14]=[CH:15][N:10]3[N:9]=2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-(4-fluorophenyl)-3-(3-(dimethylamino)-2-propenoyl)pyrazolo[1,5-a]pyridine (60 mg, 0.19 mmol), guanidinium hydrochloride (36 mg, 0.38 mmol), and K2CO3 (105 mg, 0.76 mmol) in N,N-dimethylformamide (3 mL) was stirred in a 110° C. oil bath for 8 h. Additional guanidinium hydrochloride (36 mg, 0.38 mmol) was added, and the mixture stirred in a 110° C. oil bath for 16 h. The mixture was cooled to room temperature, and water (20 mL) added. The resulting tan precipitate was collected by filtration, washed with water, air-dried, the dried under high-vacuum to afford the title compound, 0.033 g (57%). 1H NMR (CDCl3) δ 8.57 (d, 1H, J=6.0 Hz), 8.51 (d, 1H, J=8.9 Hz), 7.98 (d, 2H, J=5.7 Hz), 7.64 (m, 2H), 7.46 (m, 1H), 7.22 (m, 2H), 7.04 (m, 1H), 6.47 (d, 1H, J=5.8 Hz), 5.76 (s. 2H). MS (+ve ion electrospray) 306 (100), (MH+).

Workup

stirringthe mixture stirred in a 110° C. oil bath for 16 h
temperatureThe mixture was cooled to room temperature
filtrationThe resulting tan precipitate was collected by filtration
washwashed with water
customair-dried
customthe dried under high-vacuum

Sources & evidence

ORD record: ord-61fcdb340be6433fa2547aad67a00658
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166597B2

Reaction notes

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