1,1-Dimethylethyl 2-cyano-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate → 6,7-Dihydro-5H-pyrrolo[3,4-d]pyrimidine-2-carbonitrile

HRID 602961Notes

Reaction equation

HRID 602961 reaction equation
[C:1]([C:3]1[N:4]=[CH:5][C:6]2[CH2:11][N:10](C(OC(C)(C)C)=O)[CH2:9][C:7]=2[N:8]=1)#[N:2]>FC(F)(F)C(O)=O.ClCCl>[N:8]1[C:7]2[CH2:9][NH:10][CH2:11][C:6]=2[CH:5]=[N:4][C:3]=1[C:1]#[N:2]

Participants

4

Reactant 1

HCID 184428191,1-Dimethylethyl 2-cyano-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate

Product 1

HCID 457898156,7-Dihydro-5H-pyrrolo[3,4-d]pyrimidine-2-carbonitrile

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

A solution of tert-butyl 2-cyano-5,7-dihydro-6H-pyrrolo[3,4-d]pyrimidine-6-carboxylate (150 mg) in trifluoroacetic acid and dichloromethane (1:1, 1 mL) was stirred for one h and evaporated. The residue was purified by flash column chromatography (silica, 0-4% methanol containing 10% ammonium hydroxide in dichloromethane) to yield 6,7-dihydro-5H-pyrrolo[3,4-d]pyrimidine-2-carbonitrile.

Workup

  1. customevaporated
  2. customThe residue was purified by flash column chromatography (silica, 0-4% methanol containing 10% ammonium hydroxide in dichloromethane)

Sources & evidence

ORD record
ord-70e217c2d5f54b9d964d3c783df81afa
Source dataset
uspto-grants-2011_03
Patent number
US07906649B2

Reaction notes

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