HCID 68658989, compound → HCID 68658903, compound

HRID 2264305Notes

Reaction equation

HRID 2264305 reaction equation
[CH3:1][N:2](/[CH:4]=[C:5]1/[C:6](=O)[CH2:7][N:8]([C:10]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[CH2:9]/1)C.[CH3:30][C:31]1[CH:35]=C(N)[NH:33][N:32]=1.CC1C=C2N=C3CN(C(OC(C)(C)C)=O)CC3=CN2N=1>C(O)C>[CH3:35][C:31]1[CH:30]=[C:1]2[N:2]=[CH:4][C:5]3[CH2:9][N:8]([C:10]([C:17]4[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=4)([C:11]4[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=4)[C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[CH2:7][C:6]=3[N:33]2[N:32]=1

Participants

5

Reactant 3

HCID 68658989HCID 68658989, compoundHCID 68659021HCID 68659021, compoundHCID 178418690HCID 178418690, compound

Product 1

HCID 68658903HCID 68658903, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 383 mg (1 mmol) of (4E)-4-[(dimethylamino)methylene]-1-tritylpyrrolidin-3-one in anhydrous ethanol (3 mL) was added 116 mg (1.2 mmol) of 3-methyl-1H-pyrazol-5-amine and the reaction mixture refluxed for 48 h. The mixture was cooled to ambient temperature and the solvent evaporated in vacuo to afford a 10:1 mixture of the title compound and tert-butyl 2-methyl-5H-pyrazolo[1,5-a]pyrrolo[3,4-d]pyrimidine-6(7H)-carboxylate. The resulting regioisomers were chromatographed on a Biotage Horizon® system (silica gel, 2 to 3% methanol/methylene chloride gradient) to yield the title compound and its regioisomer as tan solids. LC/MS 417.1 (M+1).

Workup

  1. temperaturethe reaction mixture refluxed for 48 h
  2. customthe solvent evaporated in vacuo
  3. customto afford

Sources & evidence

ORD record
ord-6695ccb1a0dd4910812cb91dd371cf5a
Source dataset
uspto-grants-2010_12
Patent number
US07855206B2

Reaction notes

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