Methylamine → HCID 69037005, compound

HRID 1930483Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([C:21]3[C:32](=[O:33])[N:31]([CH3:34])[C:24]4[N:25]=[C:26](SC)[N:27]=[CH:28][C:23]=4[CH:22]=3)[CH:15]=2)=[O:12])[N:7]([CH3:35])[N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][NH2:37].C1COCC1>>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[CH:18][C:17]([CH3:20])=[C:16]([C:21]3[C:32](=[O:33])[N:31]([CH3:34])[C:24]4[N:25]=[C:26]([NH:37][CH3:36])[N:27]=[CH:28][C:23]=4[CH:22]=3)[CH:15]=2)=[O:12])[N:7]([CH3:35])[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 69036829HCID 69036829, compound

Product 1

HCID 69037005HCID 69037005, compoundYield 28%

Procedure

Using a procedure analogous to Example A1, 1-(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)-3-(4-methyl-3-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (217 mg, 0.441 mmol) and 2.0N methylamine in THF (2.2 mL, 4.41 mmol) were combined and purified by reverse phase chromatography (Biotage C18-25 column, 10-100% acetonitrile/water) and neutralized with 10% sodium carbonate to give 1-(3-tert-butyl-1-methyl-1H-pyrazol-5-yl)-3-(4-methyl-3-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (60 mg, 28% yield). 1H NMR (300 MHz, DMSO-d6): δ 1.15 (s, 9H), 2.06 (s, 3H), 2.90 (s, 3H), 3.53-3.63 (m, 6H), 6.02 (s, 1H), 7.12-7.14 (m, 1H), 7.23-7.26 (m, 1H), 7.34 (s, 1H), 7.66-7.80 (m, 2H), 8.42 (s, 1H), 8.58-8.68 (m, 1H), 8.79 (s, 1H); MS (ESI) m/z: 475.2 (M+H+).

Workup

custompurified by reverse phase chromatography (Biotage C18-25 column, 10-100% acetonitrile/water)

Sources & evidence

ORD record: ord-a354759c6afd42789c10db891429f5c1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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