6-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamine → 6-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amine

HRID 32601Notes

Reaction equation

HRID 32601 reaction equation
[CH3:1][N:2]1[C:6]([C:7]#[C:8][C:9]2[N:14]=[CH:13][N:12]=[C:11]([NH2:15])[C:10]=2[NH2:16])=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=[CH:3]1.C(Cl)Cl.CO>CN(C=O)C.[Cu]I>[CH3:1][N:2]1[C:6]([C:7]2[NH:16][C:10]3[C:11]([NH2:15])=[N:12][CH:13]=[N:14][C:9]=3[CH:8]=2)=[C:5]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:4]=[CH:3]1

Participants

5

Reactant 2

HCID 179657996-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamine2×HCID 21226129Dichloromethane methanol

Product 1

HCID 179657756-(1-Methyl-4-phenyl-1H-imidazol-5-yl)-5H-pyrrolo[3,2-d]pyrimidin-4-amineYield 6%

Reagents, catalysts & solvents 2

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 6228DimethylformamideSolvent

Procedure

6-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamine (intermediate 90) (50 mg) and CuI (3 mg) in DMF (2 mL) were heated at 110° C. under an inert atmosphere for 4 hours. The reaction mixture was loaded on to a 1 g SCX column prewashed with DCM:MeOH (3:1). The column was eluted with DCM:MeOH (3:1) and then the product eluted with 7N NH3/MeOH:DCM:MeOH (1:3:1). The product fraction was concentrated and then purified by flash chromatography on silica eluting with DCM:MeOH (9:1) to afford the title compound as a yellow solid (3 mg, 6%);

Workup

  1. washThe column was eluted with DCM:MeOH (3:1)
  2. washthe product eluted with 7N NH3/MeOH
  3. concentrationThe product fraction was concentrated
  4. custompurified by flash chromatography on silica eluting with DCM:MeOH (9:1)

Sources & evidence

ORD record
ord-23fed16ff2654534bd72d2b08f53012d
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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