Potassium Carbonate → 8-Ethynyl-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

HRID 1910945Notes

Reaction equation

HRID 1910945 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]23[NH:27][CH2:26][CH2:25][N:10]2[C:11](=[O:24])[C:12]2[N:13]([C:15]([C:18]#[C:19][Si](C)(C)C)=[CH:16][CH:17]=2)[CH2:14]3)=[CH:5][CH:4]=1.C(=O)([O-])[O-].[K+].[K+]>CO.C(Cl)Cl>[C:18]([C:15]1[N:13]2[CH2:14][C:9]3([C:6]4[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=4)[NH:27][CH2:26][CH2:25][N:10]3[C:11](=[O:24])[C:12]2=[CH:17][CH:16]=1)#[CH:19]

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 6736846710a-(4-methoxyphenyl)-8-[(trimethylsilyl)ethynyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one

Product 1

HCID 866570858-Ethynyl-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-oneYield 89%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 10a-(4-methoxyphenyl)-8-[(trimethylsilyl)ethynyl]-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one (84 mg, 0.22 mmol) in methanol (5 mL) was added potassium carbonate (60 mg, 0.43 mmol). The suspension was stirred at room temperature until the reaction was complete (monitored by LCMS). The solid was suspended in CH2Cl2, filtered and concentrated in vacuo to give a residue that was purified by flash chromatography (Biotage SP4, 12 g cartridge, CH2Cl2 3CV, gradient 0-10% MeOH in CH2Cl2 10CV). To give 8-Ethynyl-10a-(4-methoxyphenyl)-2,3,10,10a-tetrahydro-1H,5H-imidazo[1,2-a]pyrrolo[1,2-d]pyrazin-5-one as a yellow solid (60 mg, yield 89%). ESI-MI m/z [M+H]+ 308.0.

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customto give a residue that
  4. customwas purified by flash chromatography (Biotage SP4, 12 g cartridge, CH2Cl2 3CV, gradient 0-10% MeOH in CH2Cl2 10CV)

Sources & evidence

ORD record
ord-0005715d273e45d889ca84a4d370c8f4
Source dataset
uspto-grants-2013_12
Patent number
US08604034B2

Reaction notes

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