Methylamine → HCID 67063104, compound

HRID 599343Notes

Reaction equation

HRID 599343 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][C:16]3[C:11](=[N:12][C:13](SC)=[N:14][CH:15]=3)[N:10]([CH3:20])[C:9]2=[O:21])=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[N:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:29]=[C:28]([CH:37]([CH3:39])[CH3:38])[CH:27]=1)=[O:24].C1C=C(Cl)C=C(C(OO)=O)C=1.[CH3:51][NH2:52]>>[F:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]2[CH2:17][C:16]3[C:11](=[N:12][C:13]([NH:52][CH3:51])=[N:14][CH:15]=3)[N:10]([CH3:20])[C:9]2=[O:21])=[CH:4][C:3]=1[NH:22][C:23]([NH:25][C:26]1[N:30]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)[N:29]=[C:28]([CH:37]([CH3:39])[CH3:38])[CH:27]=1)=[O:24]

Participants

4

Reactant 3

HCID 6329MethylamineHCID 70297m-Chloroperbenzoic acidHCID 67063029HCID 67063029, compound

Product 1

HCID 67063104HCID 67063104, compoundYield 74%

Procedure

Using a procedure analogous to Example A2, the sulfide was oxidized with mCPBA to the sulfone and treated with methylamine to provide 1-(2-fluoro-5-(1-methyl-7-(methylamino)-2-oxo-1,2-dihydropyrimido[4,5-d]pyrimidin-3(4H)-yl)phenyl)-3-(3-isopropyl-1-phenyl-1H-pyrazol-5-yl)urea (74% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.05 (s, 1H), 8.13 (dd, J=8, 2.5 Hz, 1H), 7.96 (brs, 1H), 7.52 (m, 4H), 7.42 (m, 1H), 7.25 (dd, J=12.9 Hz, 1H), 7.00 (m, 2H), 6.34 (s, 1H), 4.56 (s, 2H), 3.25 (brs, 3H), 2.86 (m, 1H), 2.78 (d, J=5 Hz, 3H), 1.20 (d, J=6 Hz, 6H); MS (EST) m/z: 530.2 (M+H+).

Sources & evidence

ORD record
ord-3206673aa46844fbada2bb3b70fb92c2
Source dataset
uspto-grants-2011_03
Patent number
US07897762B2

Reaction notes

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