Triethylamine → 1-(2-(5-Chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-4-methylthiazol-5-yl)ethanone

HRID 1484993Notes

Reaction equation

[Cl:1][C:2]1[C:3]([NH:11][C:12]2[CH:16]=[C:15]([CH:17]3[CH2:19][CH2:18]3)[NH:14][N:13]=2)=[N:4][C:5]([C:8](=[S:10])[NH2:9])=[N:6][CH:7]=1.Cl[CH:21]([C:25](=O)[CH3:26])[C:22](=[O:24])[CH3:23].CCN(CC)CC>CCO>[Cl:1][C:2]1[C:3]([NH:11][C:12]2[CH:16]=[C:15]([CH:17]3[CH2:18][CH2:19]3)[NH:14][N:13]=2)=[N:4][C:5]([C:8]2[S:10][C:21]([C:22](=[O:24])[CH3:23])=[C:25]([CH3:26])[N:9]=2)=[N:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of crude 5-chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidine-2-carbothioamide (1.2 g, 4.1 mmol), 3-chloropentane-2,4-dione (548 mg, 4.1 mmol, 1.0 eq) and Et3N (1.0 mL) in EtOH (30 mL) was stirred at 80° C. for 2 h, then, concentrated. The residue was recrystallized with EtOH to produce 1-(2-(5-Chloro-4-(5-cyclopropyl-1H-pyrazol-3-ylamino)pyrimidin-2-yl)-4-methylthiazol-5-yl)ethanone (Compound 297) (300 mg, 20%). LC-MS (m/z)=375.0 [M+H]+; 1H NMR (400 MHz, DMSO-d6): δ 0.67-0.80 (m, 2H), 0.92-1.05 (m, 2H), 1.91-1.97 (m, 1H), 2.60 (s, 3H), 2.73 (s, 3H), 6.60 (s, 1H), 8.54 (s, 1H), 9.69 (s, 1H), 12.37 (s, 1H).

Workup

concentrationconcentrated
customThe residue was recrystallized with EtOH

Sources & evidence

ORD record: ord-f74edc8458c54598890d976471d55079
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09422271B2

Reaction notes

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