Methylamine tetrahydrofuran → HCID 69296299, compound

HRID 1930471Notes

Reaction equation

[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:20](=[O:21])[N:19]([CH3:22])[C:12]3[N:13]=[C:14](SC)[N:15]=[CH:16][C:11]=3[CH:10]=2)=[CH:4][C:3]=1[NH:23][C:24]([NH:26][C:27]1[CH:31]=[C:30]([CH:32]([CH3:34])[CH3:33])[O:29][N:28]=1)=[O:25].[CH3:35][NH2:36].C1COCC1>>[F:1][C:2]1[CH:7]=[C:6]([CH3:8])[C:5]([C:9]2[C:20](=[O:21])[N:19]([CH3:22])[C:12]3[N:13]=[C:14]([NH:36][CH3:35])[N:15]=[CH:16][C:11]=3[CH:10]=2)=[CH:4][C:3]=1[NH:23][C:24]([NH:26][C:27]1[CH:31]=[C:30]([CH:32]([CH3:34])[CH3:33])[O:29][N:28]=1)=[O:25]

Participants

Reactant 2

HCID 66615946Methylamine tetrahydrofuran

HCID 69041368HCID 69041368, compound

Product 1

HCID 69296299HCID 69296299, compoundYield 62.8%

Procedure

Following a procedure analogous to Example A1, 1-(2-fluoro-4-methyl-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(5-isopropylisoxazol-3-yl)urea (0.0635 g, 0.13 mmol) and 2.0M MeNH2/THF (0.66 ml, 1.3 mmol) were combined to afford 1-(2-fluoro-4-methyl-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)-3-(5-isopropylisoxazol-3-yl)urea (38 mg, 62% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 9.77 (s, 1H), 8.75 (brs, 1H), 8.60 (s, 1H), 7.92 (d, J=8.4 Hz, 1H), 7.80 (brq, J=4.4 Hz, 1H), 7.68 (s, 1H), 7.36 (d, J=12.4 Hz, 1H), 6.45 (s, 1H), 3.60 (s, 3H), 2.99 (septet, J=6.8 Hz, 1H), 2.90 (brd, J=4.4 Hz, 3H), 2.07 (s, 3H), 1.20 (d, J=6.8 Hz, 6H); MS (ESI) m/z: 466.2 (M+H+).

Sources & evidence

ORD record: ord-c3906f80831f483b95b6418b4ea106e1
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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