4-Chloro-6-(phenylethynyl)pyrimidin-5-amine → 4-Chloro-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine

HRID 500882Notes

Reaction equation

HRID 500882 reaction equation
[Cl:1][C:2]1[C:7]([NH2:8])=[C:6]([C:9]#[C:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:5]=[CH:4][N:3]=1>CN1C(=O)CCC1>[Cl:1][C:2]1[C:7]2[NH:8][C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=3)=[CH:9][C:6]=2[N:5]=[CH:4][N:3]=1

Participants

3

Reactant 1

HCID 594245784-Chloro-6-(phenylethynyl)pyrimidin-5-amine

Product 1

HCID 573550364-Chloro-6-phenyl-5H-pyrrolo[3,2-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

To a solution of 251 (30.8 mg, 0.134 mmol) in NMP (1.4 mL) a suspension of KH in mineral oil (35%, 31 mL, 0.268 mmol) was added in one portion. The mixture was stirred at room temperature overnight and partitioned between EtOAc and water. The organic phase was collected, dried over anhydrous Na2SO4 and concentrated. The residue was purified by flash chromatography, eluent EtOAc/hexane (1:2) to afford title compound affording 252 (22.7 mg, 74% yield). MS (m/z): 230.1 (100%) 232.1 (33%) (M+1).

Workup

  1. additionwas added in one portion
  2. custompartitioned between EtOAc and water
  3. customThe organic phase was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated
  6. customThe residue was purified by flash chromatography, eluent EtOAc/hexane (1:2)

Sources & evidence

ORD record
ord-06d335ed768f4bf5a193b67e39a0396c
Source dataset
uspto-grants-2010_08
Patent number
US07772247B2

Reaction notes

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