Methylamine → HCID 69299497, compound

HRID 1930442Notes

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[C:27]([CH3:32])=[N:28][CH:29]=[N:30][CH:31]=1)=[O:24].[CH3:33][NH2:34].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:34][CH3:33])[N:14]=[CH:15][C:10]=3[CH:9]=2)=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[C:27]([CH3:32])=[N:28][CH:29]=[N:30][CH:31]=1)=[O:24]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 69296267HCID 69296267, compound

Product 1

HCID 69299497HCID 69299497, compoundYield 38%

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-(4-methylpyrimidin-5-yl)urea (300 mg, 0.664 mmol) and 2.0 N methylamine in THF (2.3 mL, 4.53 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-(4-methylpyrimidin-5-yl)urea (75 mg, 38% yield). 1H NMR (300 MHz, DMSO-d6), δ 2.45 (s, 3H), 2.88 (s, 3 H), 3.50-3.57 (m, 3 H), 7.23-7.29 (m, 2 H), 7.67-7.79 (m, 1 H), 7.82 (s, 1 H), 8.39-8.42 (m, 1 H), 8.60 (s, 3 H), 8.68 (s, 2 H), 9.13 (m, 1 H); MS (ESI) m/z: 435.2 (M+H+).

Sources & evidence

ORD record: ord-5adcd208dc6b4ab3a5b7eaa2803632f8
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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