1H-Pyrazol-3-amine, 5-methyl- → HCID 178419098, compound

HRID 1166263Notes

Reaction equation

Cl[C:2]1[C:3]2[CH:17]=[CH:16][CH:15]=[N:14][C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1.[NH2:18][C:19]1[CH:23]=[C:22]([CH3:24])[NH:21][N:20]=1>C1COCC1>[CH3:24][C:22]1[CH:23]=[C:19]([NH:18][C:2]2[C:3]3[CH:17]=[CH:16][CH:15]=[N:14][C:4]=3[N:5]=[C:6]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[N:7]=2)[NH:20][N:21]=1

Participants

Conditions

Temperature: 65 °C

Procedure

To a solution of 4-chloro-2-phenyl-pyrido[2,3-d]pyrimidine (J. Pharm. Belg., 29, 1974, 145-148) (109 mg, 0.45 mmol) in THF (15 mL) was added 3-amino-5-methyl pyrazole (48 mg, 0.5 mmol) and the resulting mixture heated at 65° C. overnight. The mixture was cooled to room temperature and the resulting suspension was filtered and washed with Et2O. The solid was dissolved in a mixture EtOH:water and the pH adjusted to pH 7. The aqueous was extracted twice with ethyl acetate and the combined organic layers were dried (MgSO4), filtered, and concentrated in vacuo. The residue was purified by flash chromatography (SiO2, DCM-MeOH gradient) to afford IV-31 as an off-white solid (69 mg, 50%): mp 234° C.; 1H NMR (DMSO) δ 2.14 (3H, s), 5.99 (1H, s), 7.20-7.40 (3H, m), 7.40-7.50 (3H, m), 8.60 (1H, d), 8.79 (1H, d), 12.82 (1H, br s); IR (solid) 2957, 2921, 2857, 1644, 1560, 1459, 1427; MS 303.2 (M+H)+.

Workup

temperatureThe mixture was cooled to room temperature
filtrationthe resulting suspension was filtered
washwashed with Et2O
dissolutionThe solid was dissolved in a mixture EtOH
extractionThe aqueous was extracted twice with ethyl acetate
dry with materialthe combined organic layers were dried (MgSO4)
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was purified by flash chromatography (SiO2, DCM-MeOH gradient)

Sources & evidence

ORD record: ord-7e2967c5271b49c3b9e28181f10917d4
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06613776B2

Reaction notes

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