Methylamine → HCID 24810933, compound

HRID 599340Notes

Reaction equation

[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([N:20]3[CH2:29][C:28]4[C:23](=[N:24][C:25](SC)=[N:26][CH:27]=4)[N:22]([CH3:32])[C:21]3=[O:33])[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[N:7]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:53][NH2:54]>>[C:1]([C:5]1[CH:9]=[C:8]([NH:10][C:11]([NH:13][C:14]2[CH:19]=[C:18]([N:20]3[CH2:29][C:28]4[C:23](=[N:24][C:25]([NH:54][CH3:53])=[N:26][CH:27]=4)[N:22]([CH3:32])[C:21]3=[O:33])[C:17]([CH3:34])=[CH:16][C:15]=2[F:35])=[O:12])[N:7]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[N:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

Reactant 3

HCID 6329Methylamine

HCID 70297m-Chloroperbenzoic acid

HCID 67063122HCID 67063122, compound

Product 1

HCID 24810933HCID 24810933, compoundYield 66%

Procedure

Using a procedure analogous to Example A2, the sulfide was oxidized with mCPBA to the sulfone and then treated with methylamine to provide 1-(3-tert-butyl-1-phenyl-1H-pyrazol-5-yl)-3-(2-fluoro-4-methyl-5-(1-methyl-7-(methylamino)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)phenyl)urea (0.163 g, 66% yield). 1H NMR (400 MHz, DMSO-d6): δ 8.98 (s, 1H), 8.85 (brs, 1H), 8.05 (d, J=8.0 Hz, 1H), 7.94 (s, 1H), 7.52 (m, 3H), 7.42 (m, 1H), 7.18 (d, J=12 Hz, 1H), 7.02 (m, 1H), 6.38 (s, 1H), 4.53 (d, J=14 Hz, 1H), 4.33 (d, J=14 Hz, 1H), 3.25 (brs, 3H), 2.78 (d, J=5 Hz, 3H), 2.04 (s, 3H), 1.25 (s, 9H); MS (ESI) m/z: 558.3 (M+H+).

Sources & evidence

ORD record: ord-24bedfc038aa4c4f9c029f63106c4e93
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897762B2

Reaction notes

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