Methylamine → HCID 68986895, compound

HRID 1930446Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:19](=[O:20])[N:18]([CH3:21])[C:11]3[N:12]=[C:13](SC)[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:29]=[CH:28][N:27]=1)=[O:24].[CH3:38][NH2:39].C1COCC1>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:19](=[O:20])[N:18]([CH3:21])[C:11]3[N:12]=[C:13]([NH:39][CH3:38])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[CH:31]=[C:30]([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[N:29]=[CH:28][N:27]=1)=[O:24]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 69296226HCID 69296226, compound

Product 1

HCID 68986895HCID 68986895, compoundYield 54%

Procedure

Using a procedure analogous to Example A1, 1-(2-fluoro-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(6-phenylpyrimidin-4-yl)urea (265 mg, 0.516 mmol) and 2.00 N methylamine in THF (3.87 mL, 7.73 mmol) were combined to afford 1-(2-fluoro-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(6-phenylpyrimidin-4-yl)urea (139 mg, 54% yield). 1H NMR (300 MHz, DMSO-d6) δ 2.89 (m, 3H), 3.54-3.62 (m, 3H), 7.29-7.35 (m, 2H), 7.53-7.55 (m, 3H), 7.70-7.82 (m, 1H), 7.91 (s, 1H), 8.03-8.06 (m, 2H), 8.13 (s, 1H), 8.44-8.46 (s, 1H), 8.60-8.75 (m, 1H), 8.98 (s, 1H), 10.1 (br. s, 1H), 10.2 (s, 1H); MS (ESI) m/z: 497.2 (M+H+).

Sources & evidence

ORD record: ord-4571a4afadf34fd68d043882f608a1a6
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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