Pyridine → 3-(2-bromo-phenyl)-3,4-dihydro-7-[2-(p-toluenesulfonyl)oxymethyl-benzodioxane-6 yl]amino-1-methyl-pyrimido[4,5-d]pyrimidin-2 (1H)-one

HRID 9728Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([NH:18][C:19]3[CH:30]=[CH:29][C:22]4[O:23][CH:24]([CH2:27][OH:28])[CH2:25][O:26][C:21]=4[CH:20]=3)=[N:14][CH:15]=2)[N:10]([CH3:31])[C:9]1=[O:32].[S:33](Cl)([C:36]1[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=1)(=[O:35])=[O:34].N1C=CC=CC=1>C(Cl)(Cl)Cl.CN(C)C1C=CN=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[CH2:17][C:16]2[C:11](=[N:12][C:13]([NH:18][C:19]3[CH:30]=[CH:29][C:22]4[O:23][CH:24]([CH2:27][O:28][S:33]([C:36]5[CH:42]=[CH:41][C:39]([CH3:40])=[CH:38][CH:37]=5)(=[O:35])=[O:34])[CH2:25][O:26][C:21]=4[CH:20]=3)=[N:14][CH:15]=2)[N:10]([CH3:31])[C:9]1=[O:32]

Participants

Conditions

Temperature: 5 °C

Procedure

520 mg of the product from example 1 were dissolved in 20 ml CHCl3. 213 mg tosyl chloride and 13 mg 4-dimethylaminopyridine were added and the mixture was cooled to 5° C. 166 mg pyridine were added dropwise and stirring was continued at room temperature for 3 hrs. The mixture was stirred 1 hr at 60° C., then another 105 mg tosyl chloride were added and stirring was continued at room temperature for 16 hrs. The mixture was diluted with 50 ml CHCl3 and washed with 0.5 M HCl, dried and evaporated. Chromatography on silica yielded 180 mg of the title compound.

Workup

stirringThe mixture was stirred 1 hr at 60° C.
stirringstirring
waitwas continued at room temperature for 16 hrs
washwashed with 0.5 M HCl
customdried
customevaporated

Sources & evidence

ORD record: ord-2f4ba6433b594125bf21b306ef755b52
Source dataset: uspto-grants-2006_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07091345B2

Reaction notes

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