Triethylamine → 6-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamine

HRID 32603

Reaction equation

HRID 32603 reaction equation
I[C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=1[NH2:9].[C:10]([C:12]1[N:16]([CH3:17])[CH:15]=[N:14][C:13]=1[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)#[CH:11].C(N(CC)CC)C>CN(C=O)C.[Cu]I>[CH3:17][N:16]1[C:12]([C:10]#[C:11][C:2]2[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[C:3]=2[NH2:9])=[C:13]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:14]=[CH:15]1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 179658065-Ethynyl-1-methyl-4-phenyl-1H-imidazole2×HCID 179658946-Iodopyrimidine-4,5-diamine2×

Product 1

HCID 179657996-[(1-Methyl-4-phenyl-1H-imidazol-5-yl)ethynyl]pyrimidine-4,5-diamineYield 76.4%

Reagents, catalysts & solvents 2

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

Procedure

6-Iodopyrimidine-4,5-diamine (Intermediate 89) (50 mg), CuI (2 mg), PdCl2dppf (16 mag), 5-ethynyl-1-methyl-4-phenyl-1H-imidazole (intermediate 26) (77 mg), and triethylamine (0.33 mL) in DMF (7 mL) were mixed together and then degassed. The reaction mixture was allowed to stir at ambient temperature under an inert atmosphere for 24 hours. The reaction mixture was filtered through diatomaceous earth, washing well with DCM and then MeCN. The organics were concentrated and the residue purified by chromatography on silica eluting with DCM:MeOH (9:1) to afford the title compound as a yellow solid (47 mg, 76%);

Workup

  1. customdegassed
  2. filtrationThe reaction mixture was filtered through diatomaceous earth
  3. washwashing well with DCM
  4. concentrationThe organics were concentrated
  5. customthe residue purified by chromatography on silica eluting with DCM:MeOH (9:1)

Sources & evidence

ORD record
ord-d720884f28ce43b4bd80e03c3ddae8c0
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Linked notes

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