Methylamine tetrahydrofuran → HCID 69297694, compound

HRID 1930455Notes

Reaction equation

[C:1]([C:5]1[S: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]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])=[N:7][N:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:36][NH2:37].C1COCC1>>[C:1]([C:5]1[S: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:37][CH3:36])[N:26]=[CH:27][C:22]=4[CH:21]=3)[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])=[N:7][N:6]=1)([CH3:2])([CH3:3])[CH3:4]

Participants

Reactant 2

HCID 66615946Methylamine tetrahydrofuran

HCID 69298841HCID 69298841, compound

Product 1

HCID 69297694HCID 69297694, compoundYield 93.2%

Procedure

Using a procedure analogous to Example A1, 1-(5-t-butyl-1,3,4-thiadiazol-2-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.345 g, 0.672 mmol) and 2.00M MeNH2/THF (3.36 ml, 6.72 mmol) were combined to afford 1-(5-tert-butyl-1,3,4-thiadiazol-2-yl)-3-(2-fluoro-4-methyl-5-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (0.311 g, 93% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): δ 7.822-7.75 (m, 3H), 7.69 (s, 1H), 7.39-7.37 (m, 1H), 7.34-7.30 (m, 1H), 7.16 (d, J=12.0 Hz, 1H), 2.90 (brd, J=4.8 Hz, 3H), 2.35 (s, 3H), 2.09 (s, 3H), 1.34 (s, 9H); MS (ESI) m/z: 497.0 (M+H).

Sources & evidence

ORD record: ord-7cb68277c8174256897f250777672b10
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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