Methylamine → HCID 69036476, compound

HRID 1930467Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25](SC)[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([Cl:34])=[CH:16][C:15]=2[F:35])=[O:12])[N:7]([CH3:36])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:37][NH2:38].C1COCC1>>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([C:20]3[C:31](=[O:32])[N:30]([CH3:33])[C:23]4[N:24]=[C:25]([NH:38][CH3:37])[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([Cl:34])=[CH:16][C:15]=2[F:35])=[O:12])[N:7]([CH3:36])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 69039109HCID 69039109, compound

Product 1

HCID 69036476HCID 69036476, compoundYield 23%

Procedure

Using a procedure analogous to example A1, 1-(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)-3-(4-chloro-2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.2, 0.38 mmol) and 2 M methylamine in THF (3 eq) were combined and purified via C-18 chromatography to provide 1-(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)-3(4-chloro-2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea as a white solid (0.045 g, 23% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.95 (brs, 2H), 8.61 (s, 1H), 8.17 (d, J=8.8 Hz, 1H), 7.87 (brs, 1H), 7.75 (s, 1H), 7.55 (d, J=10.8 Hz, 1H), 6.04 (s, 1H), 3.58-3.51 (m, 6H), 2.90 (s, 3H), 1.16 (s, 9H); MS (ESI) m/z: 513.3 (M+H+).

Workup

custompurified via C-18 chromatography

Sources & evidence

ORD record: ord-23b5203c88c545bfb36c5cefde52d79e
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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