Water → HCID 67116641, compound

HRID 1193201Notes

Reaction equation

HRID 1193201 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][N:14]([C:17]([C:19]4[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=4[C:26]4[NH:30][N:29]=[CH:28][CH:27]=4)=[O:18])[CH2:15]3)[CH2:10]2)[N:3]=1.[H-].[Na+].[CH3:33]I.O>CN(C=O)C>[CH3:1][C:2]1[CH:7]=[C:6]([CH3:8])[N:5]=[C:4]([N:9]2[C@@H:16]3[C@@H:11]([CH2:12][CH2:13][N:14]([C:17]([C:19]4[CH:24]=[C:23]([F:25])[CH:22]=[CH:21][C:20]=4[C:26]4[CH:27]=[CH:28][N:29]([CH3:33])[N:30]=4)=[O:18])[CH2:15]3)[CH2:10]2)[N:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 52920283HCID 52920283, compound

Product 1

HCID 67116641HCID 67116641, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
-5 °C

Procedure

A solution of the (1R,6S)-8-(4,6-dimethylpyrimidin-2-yl)-3-{[5-fluoro-2-(1H-pyrazol-3-yl)phenyl]carbonyl}-3,8-diazabicyclo[4.2.0]octane (Example 171) in DMF was treated with NaH at RT and stirred for 15 minutes until no more gas evolution occurred. The solution was cooled to −5° C. and then treated with MeI. Reaction allowed to stir for 20 min and then worked up by the addition of water followed by multiple extractions with EtOAc. Purified on 12 g SiO2 with 0-3.5% NH3 MeOH in CH2Cl2. MS (ESI) mass calcd. for C23H25FN6O, 420.5; m/z found, 421.2 [M+H]+.

Workup

  1. customReaction
  2. stirringto stir for 20 min
  3. extractionfollowed by multiple extractions with EtOAc
  4. customPurified on 12 g SiO2 with 0-3.5% NH3 MeOH in CH2Cl2

Sources & evidence

ORD record
ord-7e49d8c9895a4fcc8df04019f5958c5f
Source dataset
uspto-grants-2014_03
Patent number
US08680275B2

Reaction notes

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