N-[4-(4-amino-2,5-difluorophenoxy)-6-chloropyrimidin-2-yl]acetamide → N-[4-(4-amino-2,5-difluorophenoxy)pyrimidin-2-yl]acetamide

HRID 476362Notes

Reaction equation

[NH2:1][C:2]1[C:19]([F:20])=[CH:18][C:5]([O:6][C:7]2[CH:12]=[C:11](Cl)[N:10]=[C:9]([NH:14][C:15](=[O:17])[CH3:16])[N:8]=2)=[C:4]([F:21])[CH:3]=1>[Pd].CO>[NH2:1][C:2]1[C:19]([F:20])=[CH:18][C:5]([O:6][C:7]2[CH:12]=[CH:11][N:10]=[C:9]([NH:14][C:15](=[O:17])[CH3:16])[N:8]=2)=[C:4]([F:21])[CH:3]=1

Participants

Conditions

Temperature: 15 °C

Procedure

A mixture of N-[4-(4-amino-2,5-difluoro-phenoxy)-6-chloro-pyrimidin-2-yl]-acetamide (3.3 g, 10.5 mmol) and palladium on carbon (1.0 g, 10%) in methanol (100 mL) was stirred under H2 (1 atm) at 15° C. for 4 h. The reaction mixture was filtered and the filtrate was concentrated under reduced pressure to give N-[4-(4-amino-2,5-difluoro-phenoxy)-pyrimidin-2-yl]-acetamide (2.4 g, 82% yield) as a pale yellow solid. 1HNMR (400 MHz, DMSO-d6): δ10.37 (s, 1H), 8.44 (d, J=5.7 Hz, 1H), 7.15 (dd, J=11.4 Hz, J=4.8 Hz, 1H) 6.71 (d, J=5.7 Hz, 1H), 6.65 (dd. J=12.3 Hz, J=8.4 Hz, 1H), 5.40 (s, 2H), 1.99 (s, 3H); MS (ESI) m/z: 281.2[M+H]+.

Workup

filtrationThe reaction mixture was filtered
concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record: ord-2ca6a29cbc5741bebde07e165db9588d
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08637672B2

Reaction notes

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