Methylamine → HCID 67063103, compound

HRID 599342Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:27][C:26]4[C:21](=[N:22][C:23](SC)=[N:24][CH:25]=4)[N:20]([CH3:30])[C:19]3=[O:31])[CH:15]=[CH:14][C:13]=2[F:32])=[O:10])=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:48][NH2:49]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9]([NH:11][C:12]2[CH:17]=[C:16]([N:18]3[CH2:27][C:26]4[C:21](=[N:22][C:23]([NH:49][CH3:48])=[N:24][CH:25]=4)[N:20]([CH3:30])[C:19]3=[O:31])[CH:15]=[CH:14][C:13]=2[F:32])=[O:10])=[CH:4][C:3]=1[C:33]([F:36])([F:35])[F:34]

Participants

Reactant 3

HCID 6329Methylamine

HCID 70297m-Chloroperbenzoic acid

HCID 67062987HCID 67062987, compound

Product 1

HCID 67063103HCID 67063103, compoundYield 16%

Procedure

Using a procedure analogous to Example A2, 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-5-(1-methyl-7-(methylthio)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)phenyl)urea was oxidized with mCPBA to the sulfone and then treated with methylamine to provide 1-(4-chloro-3-(trifluoromethyl)phenyl)-3-(2-fluoro-5-(1-methyl-7-(methylamino)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)phenyl)urea (0.045 g, 16% yield). 1H NMR (400 MHz, DMSO-d6: δ 9.55 (s, 1H), 8.77 (s, 1H), 8.12 (d, J=2.5 Hz, 1H)), 8.09 (dd, J=8, 2.5 Hz, 1H), 7.96 (brs, 1H), 7.59 (m, 2H), 7.28 (dd, J=12.9 Hz, 1H), 7.01 (m, 2H), 5.74 (s, 1H), 4.58 (s, 2H), 3.28 (brs, 3H), 2.78 (d, J=5 Hz, 3H); MS (ESI) m/z: 524.0 (M+H+)

Sources & evidence

ORD record: ord-923e70916aae4ef1976a7b1d2d479a91
Source dataset: uspto-grants-2011_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07897762B2

Reaction notes

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