Methyl iodide → HCID 68109890, compound

HRID 525077Notes

Reaction equation

HRID 525077 reaction equation
[H-].[Na+].[CH3:3][C:4]1[C:12]2[C:11]([O:13][CH:14]3[CH2:19][CH2:18][CH:17]([NH:20][C:21](=[O:27])[O:22][C:23]([CH3:26])([CH3:25])[CH3:24])[CH2:16][CH2:15]3)=[N:10][CH:9]=[N:8][C:7]=2[S:6][C:5]=1[CH3:28].I[CH3:30]>CN(C)C=O>[CH3:3][C:4]1[C:12]2[C:11]([O:13][CH:14]3[CH2:15][CH2:16][CH:17]([N:20]([CH3:30])[C:21](=[O:27])[O:22][C:23]([CH3:24])([CH3:25])[CH3:26])[CH2:18][CH2:19]3)=[N:10][CH:9]=[N:8][C:7]=2[S:6][C:5]=1[CH3:28]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 68109950HCID 68109950, compound

Product 1

HCID 68109890HCID 68109890, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Sodium hydride (220 mg, 9.17 mmol, 3.46 equiv) was added to a solution of tert-butyl N-[4-([5,6-dimethylthieno[2,3-d]pyrimidin-4-yl]oxy)cyclohexyl]carbamate (1.0 g, 2.65 mmol, 1.00 equiv) in N,N-dimethylformamide (15 mL) in several batches at 0° C. and the reaction mixture was stirred for 30 min. To this reaction mixture was added iodomethane (450 mg, 3.17 mmol, 1.20 equiv) dropwise at room temperature. The reaction mixture was stirred for 1 h at 30° C. and then quenched by the addition of 5 mL of water. The resulting solution was diluted with 50 mL of water, extracted with 2×50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 2×50 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum to give 0.6 g (58%) of tert-butyl N-[4-([5,6-dimethylthieno[2,3-d]pyrimidin-4-yl]oxy)cyclohexyl]-N-methylcarbamate as a brown solid.

Workup

  1. stirringThe reaction mixture was stirred for 1 h at 30° C.
  2. customquenched by the addition of 5 mL of water
  3. additionThe resulting solution was diluted with 50 mL of water
  4. extractionextracted with 2×50 mL of ethyl acetate
  5. washThe resulting mixture was washed with 2×50 mL of brine
  6. dry with materialThe mixture was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-35a689e8f09e44578c5765f18f70ad9d
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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