Potassium Carbonate → HCID 86614255, compound

HRID 222196Notes

Reaction equation

HRID 222196 reaction equation
C(=O)([O-])[O-].[K+].[K+].[CH3:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([CH:15]2[O:20][C@H:19]3[CH2:21][C@H:22]([N:24]4[C:28]5[N:29]=[CH:30][N:31]=[C:32]([CH3:33])[C:27]=5[C:26]([C:34]#[C:35][Si](C)(C)C)=[CH:25]4)[CH2:23][C@H:18]3[CH2:17][O:16]2)=[CH:11][CH:10]=1>CO.CCOC(C)=O>[C:34]([C:26]1[C:27]2[C:32]([CH3:33])=[N:31][CH:30]=[N:29][C:28]=2[N:24]([C@H:22]2[CH2:21][C@@H:19]3[O:20][CH:15]([C:12]4[CH:11]=[CH:10][C:9]([O:8][CH3:7])=[CH:14][CH:13]=4)[O:16][CH2:17][C@@H:18]3[CH2:23]2)[CH:25]=1)#[CH:35]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 66618236HCID 66618236, compound

Product 1

HCID 86614255HCID 86614255, compoundYield 81.2%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

Potassium carbonate (191 mg, 1.38 mmol) was added to a solution of 7-[(4aS,6R,7aS)-2-(4-methoxyphenyl)hexahydrocyclopenta[d][1,3]dioxin-6-yl]-4-methyl-5-[(trimethylsilyl)ethynyl]-7H-pyrrolo[2,3-d]pyrimidine (314 mg, 0.680 mmol) in MeOH (10.0 mL), and the mixture was stirred at rt overnight. The reaction mixture was diluted with EtOAc, washed with saturated aqueous sodium bicarbonate solution, dried over MgSO4, filtered, and concentrated in vacuo to afford the title compound as an oil (215 mg, 81%). LC/MS: Rt=1.94 min, ES+ 390 (AA standard).

Workup

  1. washwashed with saturated aqueous sodium bicarbonate solution
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9e7d4c873d6744c88843786f29a7b608
Source dataset
uspto-grants-2012_06
Patent number
US08207177B2

Reaction notes

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