Methylamine → N-[4-Methyl-3-(1-methyl-7-methylamino-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-phenyl]-3-trifluoromethyl-benzamide

HRID 2222255Notes

Reaction equation

CS([C:4]1[N:9]=[C:8]2[N:10]([CH3:36])[C:11](=[O:35])[N:12]([C:15]3[CH:16]=[C:17]([NH:22][C:23](=[O:34])[C:24]4[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:33])([F:32])[F:31])[CH:25]=4)[CH:18]=[CH:19][C:20]=3[CH3:21])[C:13](=[O:14])[C:7]2=[CH:6][N:5]=1)=O.[CH3:37][NH2:38]>C1COCC1>[CH3:21][C:20]1[CH:19]=[CH:18][C:17]([NH:22][C:23](=[O:34])[C:24]2[CH:29]=[CH:28][CH:27]=[C:26]([C:30]([F:32])([F:31])[F:33])[CH:25]=2)=[CH:16][C:15]=1[N:12]1[C:13](=[O:14])[C:7]2[C:8](=[N:9][C:4]([NH:38][CH3:37])=[N:5][CH:6]=2)[N:10]([CH3:36])[C:11]1=[O:35]

Participants

Conditions

Temperature: 60 °C

Procedure

N-[3-(7-Methanesulfinyl-1-methyl-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-4-methyl-phenyl]-3-trifluoromethyl-benzamide (30 mg, 58 μmol) is dissolved in 2 M methylamine solution (1 mL) in THF and the mixture is stirred for 1 h at 60° C. The reaction mixture is concentrated, dissolved in DMSO, and purified by preparative LCMS to give N-[4-Methyl-3-(1-methyl-7-methylamino-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-phenyl]-3-trifluoromethyl-benzamide (20 mg, 71%); 1H NMR 400 MHz (DMSO-d6) δ 10.70 (s, 1H), 8.95 (s, 0.33H), 8.85 (s, 0.66H), 8.39 (m, 3H), 8.11 (d, 1H), 7.93 (t, 1H), 7.84 (m, 2H), 7.49 (d, 1H), 3.65 (d, 2H), 3.58 (s, 1H), 3.08 (m, 3H), 2.17 (s, 3H); MS m/z 485.3 (M+1).

Workup

concentrationThe reaction mixture is concentrated
dissolutiondissolved in DMSO
custompurified by preparative LCMS

Sources & evidence

ORD record: ord-6f09680496a747e79b059967f8d98930
Source dataset: uspto-grants-2008_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07371750B2

Reaction notes

Loading…