Methylamine → HCID 69298857, compound

HRID 1930482Notes

Reaction equation

HRID 1930482 reaction equation
[C:1]([C:5]1[O:9][N:8]=[C:7]([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:6]=1)([CH3:4])([CH3:3])[CH3:2].[CH3:35][NH2:36]>C1COCC1>[C:1]([C:5]1[O:9][N:8]=[C:7]([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:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6329MethylamineHCID 69088972HCID 69088972, compound

Product 1

HCID 69298857HCID 69298857, compoundYield 32%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Using general method B, the carbamate of 5-t-butylisoxazol-3-amine (108 mg, 0.480 mmol) and Example A44 (150 mg, 0.480 mmol) were combined to give the intermediate sulfide, 1-(5-tert-butylisoxazol-3-yl)-3-(4-methyl-3-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (35 mg, 15% yield). Using a procedure analogous to Example A1, 1-(5-tert-butylisoxazol-3-yl)-3-(4-methyl-3-(8-methyl-2-(methylthio)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (158 mg, 0.330 mmol) and 2.0N solution of methylamine in THF (1.7 mL) were combined and purified by chromatography (Biotage Si-25 column, 60-100% ethyl acetate/Hex) to afford 1-(5-tert-butylisoxazol-3-yl)-3-(4-methyl-3-(8-methyl-2-(methylamino)-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidin-6-yl)phenyl)urea (49 mg, 32% yield). 1H NMR (300 MHz, DMSO-d6): δ 1.26 (s, 9H), 2.06 (s, 3H), 2.90 (s, 3H), 3.53-3.60 (m, 3H), 6.46 (s, 1H), 7.14-7.16 (m, 1H), 7.26-7.28 (m, 1H), 7.32 (s, 1H), 7.67 (s, 1H), 7.65-7.80 (br m, 1H), 8.60-8.65 (m, 1H), 8.72 (s, 1H), 9.47 (s, 1H); MS (ESI) m/z: 462.0 (M+H+).

Workup

  1. custompurified by chromatography (Biotage Si-25 column, 60-100% ethyl acetate/Hex)

Sources & evidence

ORD record
ord-8f220674d61e4fe1ab90c506dd67f899
Source dataset
uspto-grants-2012_05
Patent number
US08188113B2

Reaction notes

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