Sodium hydride → 4-{(4S)-6-Methyl-3-(methylsulfonyl)-2,5-dioxo-1-[3-(trifluoromethyl)phenyl]-2,3,4,5,6,7-hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4-yl}-3-(methylsulfonyl)benzonitrile

HRID 336940Notes

Reaction equation

[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[C@@H:8]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=3[S:20]([CH3:23])(=[O:22])=[O:21])[NH:7][C:6](=[O:24])[N:5]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:33])[F:32])[CH:26]=3)[C:4]=2[CH2:3]1.[H-].[Na+].[CH3:37][S:38](Cl)(=[O:40])=[O:39]>>[CH3:1][N:2]1[C:10](=[O:11])[C:9]2[C@@H:8]([C:12]3[CH:19]=[CH:18][C:15]([C:16]#[N:17])=[CH:14][C:13]=3[S:20]([CH3:23])(=[O:21])=[O:22])[N:7]([S:38]([CH3:37])(=[O:40])=[O:39])[C:6](=[O:24])[N:5]([C:25]3[CH:30]=[CH:29][CH:28]=[C:27]([C:31]([F:34])([F:32])[F:33])[CH:26]=3)[C:4]=2[CH2:3]1

Participants

Reactant 3

HCID 24758Sodium hydride

HCID 31297Methanesulfonyl chloride

HCID 581336784-{(4S)-6-methyl-2,5-dioxo-1-[3-(trifluoromethyl)phenyl]-2,3,4,5,6,7-hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4-yl}-3-(methylsulfonyl)benzonitrile

Product 1

HCID 581337744-{(4S)-6-Methyl-3-(methylsulfonyl)-2,5-dioxo-1-[3-(trifluoromethyl)phenyl]-2,3,4,5,6,7-hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4-yl}-3-(methylsulfonyl)benzonitrile

Procedure

Analogously to the preparation of Example 27, 4-{(4S)-6-methyl-2,5-dioxo-1-[3-(trifluoromethyl)phenyl]-2,3,4,5,6,7-hexahydro-1H-pyrrolo[3,4-d]pyrimidin-4-yl}-3-(methylsulfonyl)benzonitrile (20 mg, 41 μmol; Example 35), sodium hydride (60%, 2.3 mg, 57 μmol) and methanesulfonyl chloride (6.5 mg, 57 μmol) were reacted with one another for 2 h. The title compound was obtained as a colorless solid (1.7 mg, 7% of theory). In addition, 6.4 mg (32% of theory) of the starting material were recovered.

Workup

customwere reacted with one another for 2 h

Sources & evidence

ORD record: ord-095f3ca2cf354af1934270cec9ac7cc5
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889700B2

Reaction notes

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