N-methyl-2-pyrrolidone → 4-(Bicyclo[1.1.1]pentan-1-ylamino)-2-chloropyrimidine-5-carboxamide

HRID 2201985Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([C:9]([NH2:11])=[O:10])=[CH:4][N:3]=1.Cl.[C:13]12([NH2:18])[CH2:17][CH:15]([CH2:16]1)[CH2:14]2.C(=O)(O)[O-].[Na+].CN1C(=O)CCC1>O>[C:13]12([NH:18][C:6]3[C:5]([C:9]([NH2:11])=[O:10])=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=3)[CH2:17][CH:15]([CH2:16]1)[CH2:14]2

Participants

Conditions

Temperature: 25 °C

Procedure

A mixture of 2,4-dichloro-pyrimidine-5-carboxamide (2 g), bicyclo[1.1.1]pentan-1-amine hydrochloride (1.18 g), sodium bicarbonate (1.75 g), and NMP (10 mL) was stirred at 25° C. for 24 h. Water (10 mL) was charged maintaining the reaction temperature less than 30° C., and the mixture was stirred at 25° C. for 2 h. The suspension was filtered, and washed with NMP:water (1:1 10 mL), then water (2×10 mL), and dried in a vacuum oven at 40° C. with nitrogen sweep to give 4-(bicyclo[1.1.1]pentan-1-ylamino)-2-chloropyrimidine-5-carboxamide as a white solid (1.97 g, 83% yield). 1H NMR (DMSO-d6) δ 2.14 (s, 6H), 2.51-2.53 (m, 1H), 7.76 (br. s., 1H), 8.23 (br. s., 1H), 8.60 (s, 1H), 9.57 (s, 1H).

Workup

temperaturemaintaining the reaction temperature less than 30° C.
stirringthe mixture was stirred at 25° C. for 2 h
filtrationThe suspension was filtered
washwashed with NMP:water (1:1 10 mL)
dry with materialwater (2×10 mL), and dried in a vacuum oven at 40° C. with nitrogen sweep

Sources & evidence

ORD record: ord-71fb34a351894cdfb948106f89c586eb
Source dataset: uspto-grants-2016_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09365524B2

Reaction notes

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