HCID 22125146, compound → HCID 22125113, compound

HRID 1858277Notes

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]([S:18]([CH3:21])(=[O:20])=[O:19])=[N:14][CH:15]=2)[N:10]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28]OS(C)(=O)=O)[CH:23]=2)[C:9]1=[O:34].[C:35]1(=[O:45])[NH:39][C:38](=[O:40])[C:37]2=[CH:41][CH:42]=[CH:43][CH:44]=[C:36]12.[K]>CN(C)C=O>[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]([S:18]([CH3:21])(=[O:20])=[O:19])=[N:14][CH:15]=2)[N:10]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([CH2:28][N:39]3[C:35](=[O:45])[C:36]4=[CH:44][CH:43]=[CH:42][CH:41]=[C:37]4[C:38]3=[O:40])[CH:23]=2)[C:9]1=[O:34]

Participants

Conditions

Temperature: 90 °C

Procedure

A solution of 250 mg (0.44 mmol) of 3-(2-bromophenyl)-3,4-dihydro-7-(methanesulfonyl)-1-[3-(methanesulfonyloxymethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one in 10 ml of dimethylformamide was treated with 111 mg (0.6 mmol) of potassium phthalimide and the mixture heated at 90° C. for 1 hour then cooled and evaporated. The residue was partitioned between 30 ml of dichloromethane and 30 ml of water. The organic phase was collected, dried over magnesium sulfate, filtered and evaporated to afford 270 mg (99%) of 3-(2-bromophenyl)-3,4-dihydro-7-(methanesulfonyl)-1-[3-(phthalimidomethyl)phenyl]pyrimido[4,5-d]pyrimidin-2(1H)-one as a white solid. [Mass spectrum (ESI) MH+ =618].

Workup

temperaturethen cooled
customevaporated
customThe residue was partitioned between 30 ml of dichloromethane and 30 ml of water
customThe organic phase was collected
dry with materialdried over magnesium sulfate
filtrationfiltered
customevaporated

Sources & evidence

ORD record: ord-7dbd74ee4df34987aebe76c117d5b4cb
Source dataset: uspto-grants-2000_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06150373

Reaction notes

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