Water → 4-(1-(3-(Difluoromethyl)phenyl)-3-methyl-2,5-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile

HRID 927240Notes

Reaction equation

HRID 927240 reaction equation
[H-].[Na+].[F:3][CH:4]([F:30])[C:5]1[CH:6]=[C:7]([N:11]2[C:16]3[CH2:17][CH2:18][C:19](=[O:20])[C:15]=3[CH:14]([C:21]3[CH:28]=[CH:27][C:24]([C:25]#[N:26])=[CH:23][CH:22]=3)[NH:13][C:12]2=[O:29])[CH:8]=[CH:9][CH:10]=1.[CH3:31]I.O>O1CCCC1>[F:30][CH:4]([F:3])[C:5]1[CH:6]=[C:7]([N:11]2[C:16]3[CH2:17][CH2:18][C:19](=[O:20])[C:15]=3[CH:14]([C:21]3[CH:22]=[CH:23][C:24]([C:25]#[N:26])=[CH:27][CH:28]=3)[N:13]([CH3:31])[C:12]2=[O:29])[CH:8]=[CH:9][CH:10]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 903108234-(1-(3-(Difluoromethyl)phenyl)-2,5-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)benzonitrile

Product 1

HCID 903108764-(1-(3-(Difluoromethyl)phenyl)-3-methyl-2,5-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium hydride (60% in mineral oil, 13 mg, 0.32 mmol) is added to a solution of 4-(1-(3-(difluoromethyl)phenyl)-2,5-dioxo-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]-pyrimidin-4-yl)benzonitrile (example 11, 100 mg, 0.26 mmol) in tetrahydrofuran. After 20 min methyl iodide (22 μL, 0.35 mmol) is added and the mixture is stirred at room temperature over night. Water is added and the mixture is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 55 mg; ESI mass spectrum [M+H]+=394; Retention time HPLC: 0.74 min (005_CA01).

Workup

  1. customthe mixture is purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  2. custom0.74 min (005_CA01)

Sources & evidence

ORD record
ord-00ca8f0cc3c648989dcb370a73ead82d
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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