Methyl iodide → HCID 90311027, compound

HRID 927242Notes

Reaction equation

HRID 927242 reaction equation
[C:1](=[O:4])([O-])[O-].[Cs+].[Cs+].O=[C:8]1[N:13]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([C:20]([F:23])([F:22])[F:21])[CH:15]=2)[C:12]2[CH2:24][CH2:25][C:26](=[O:27])[C:11]=2[CH:10]([C:28]2[CH:35]=[CH:34][C:31]([C:32]#[N:33])=[CH:30][CH:29]=2)[NH:9]1.CI>CN(C)C=O>[CH3:8][N:9]1[CH:10]([C:28]2[CH:29]=[CH:30][C:31]([C:32]#[N:33])=[CH:34][CH:35]=2)[C:11]2[C:26](=[O:27])[CH2:25][CH2:24][C:12]=2[N:13]([C:14]2[CH:19]=[CH:18][N:17]=[C:16]([C:20]([F:22])([F:21])[F:23])[CH:15]=2)[C:1]1=[O:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 90310960HCID 90310960, compound

Product 1

HCID 90311027HCID 90311027, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (82 mg, 0.25 mmol) is added to a solution of 4-(2,5-Dioxo-1-(2-(tri-fluoromethyl)pyridin-4-yl)-2,3,4,5,6,7-hexahydro-1H-cyclopenta[d]pyrimidin-4-yl)benzonitrile (example 15.5, 50 mg, 0.13 mmol) in N,N-dimethylformamide (1.0 mL). Methyl iodide (28 mg, 0.20 mmol) is added, and the mixture is stirred at room temperature for 1 h and purified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA). Yield: 43 mg; ESI mass spectrum [M+H]+=413; Retention time HPLC: 0.78 min (005_CA01).

Workup

  1. custompurified by reversed phase HPLC (Waters SunFire™-C18, gradient of acetonitrile in water, 0.1% TFA)
  2. custom0.78 min (005_CA01)

Sources & evidence

ORD record
ord-9497a7f2ffbe4f57bb6a10984b1f56a2
Source dataset
uspto-grants-2016_03
Patent number
US09290459B1

Reaction notes

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