Methylamine → HCID 69296324, compound

HRID 1930475Notes

Reaction equation

[C:1]([N: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])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH3:35][NH2:36].C1COCC1>>[C:1]([N: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:36][CH3:35])[N:27]=[CH:28][C:23]=4[CH:22]=3)[CH:15]=2)=[O:12])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6329Methylamine

HCID 8028Tetrahydrofuran

HCID 69298120HCID 69298120, compound

Product 1

HCID 69296324HCID 69296324, compoundYield 80%

Procedure

Using general method D, Example B30 (150 mg, 0.585 mmol) and Example A44 (165 mg, 0.585 mmol) were combined to give the intermediate sulfide, 1-(1-tert-butyl-1H-pyrazol-4-yl)-3-(4-methyl-3-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (56 mg, 24% yield). Using a procedure analogous to Example A1, the sulfide (56 mg, 0.117 mmol) was combined with 2.0N methylamine in THF (0.59 mL, 1.173 mmol) to afford the desired product, 1-(1-tert-butyl-1H-pyrazol-4-yl)-3-(4-methyl-3-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (43 mg, 80% yield). 1H NMR (300 MHz, DMSO-d6), δ 1.22 (s, 9H), 2.06 (s, 3H), 2.90 (s, 3H), 3.53-3.60 (m, 3H), 6.01 (s, 1H), 7.14-7.16 (d, 1H), 7.27-7.29 (d, 1H), 7.34 (s, 1H), 7.67 (s, 1H), 7.68-7.81 (m, 1H), 8.60-8.65 (m, 1H), 8.74 (s, 1H), 10.06 (s, 1H); MS (ESI) m/z: 461.2 (M+H+).

Sources & evidence

ORD record: ord-f414056d0aae49babef6aab240ff9b92
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08188113B2

Reaction notes

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