Dimethylformamide → 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

HRID 1988599Notes

Reaction equation

HRID 1988599 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][C:9](=[O:20])[C:10]2[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:19])([F:18])[F:17])[CH:11]=2)=[CH:4][C:3]=1[N:21]1[C:30](=[O:31])[C:29]2[C:24](=[N:25][C:26]([S:32][CH3:33])=[N:27][CH:28]=2)[N:23]([CH3:34])[C:22]1=[O:35].CN(C=[O:40])C.ClC1C=C(C=CC=1)C(OO)=O>C(Cl)(Cl)Cl>[CH3:33][S:32]([C:26]1[N:25]=[C:24]2[N:23]([CH3:34])[C:22](=[O:35])[N:21]([C:3]3[CH:4]=[C:5]([NH:8][C:9](=[O:20])[C:10]4[CH:15]=[CH:14][CH:13]=[C:12]([C:16]([F:17])([F:18])[F:19])[CH:11]=4)[CH:6]=[CH:7][C:2]=3[CH3:1])[C:30](=[O:31])[C:29]2=[CH:28][N:27]=1)=[O:40]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 70297m-Chloroperbenzoic acidHCID 68527350N-[4-Methyl-3-(1-methyl-7-methylsulfanyl-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-phenyl]-3-trifluoromethyl-benzamide

Product 1

HCID 68522438N-[3-(7-Methanesulfinyl-1-methyl-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-4-methyl-phenyl]-3-trifluoromethyl-benzamideYield 88%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred solution of N-[4-Methyl-3-(1-methyl-7-methylsulfanyl-2,4-dioxo-1,4-dihydro-2H-pyrimido[4,5-d]pyrimidin-3-yl)-phenyl]-3-trifluoromethyl-benzamide (184 mg, 0.37 mmol) in the mixed solvent of DMF (4 mL) and chloroform (4 mL) is added m-chloroperoxybenzoic acid (77% max., 97 mg, 44 mmol) and the mixture is stirred for 1 h at room temperature. The mixture is diluted with chloroform, and washed with 5% aqueous Na2S2O3 solution and saturated NaHCO3 solution. The organic layer is dried over MgSO4 and concentrated under reduced pressure to give 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 (167 mg, 88%).

Workup

  1. washwashed with 5% aqueous Na2S2O3 solution and saturated NaHCO3 solution
  2. dry with materialThe organic layer is dried over MgSO4
  3. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-d36662c6911741a1b2d0a56a3294d4f1
Source dataset
uspto-grants-2010_01
Patent number
US07642255B2

Reaction notes

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