2-(2-ethynyl-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine → 2-(2-Ethyl-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine

HRID 32553Notes

Reaction equation

HRID 32553 reaction equation
[C:1]([C:3]1[N:4]([CH3:24])[C:5]([C:14]2[S:15][C:16]3[N:17]=[CH:18][N:19]=[C:20]([NH2:23])[C:21]=3[N:22]=2)=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1)#[CH:2]>[Pd].CCOC(C)=O>[CH2:1]([C:3]1[N:4]([CH3:24])[C:5]([C:14]2[S:15][C:16]3[N:17]=[CH:18][N:19]=[C:20]([NH2:23])[C:21]=3[N:22]=2)=[C:6]([C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=2)[N:7]=1)[CH3:2]

Participants

4

Reactant 1

HCID 866016402-(2-ethynyl-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine2×

Product 1

HCID 691965812-(2-Ethyl-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amineYield 32.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

10% Palladium on carbon (6 mg) was added to a solution of 2-(2-ethynyl-1-methyl-4-phenyl-1H-imidazol-5-yl)[1,3]thiazolo[5,4-d]pyrimidin-7-amine (Intermediate 46) (6 mg) in EtOAc (20 mL) under an inert atmosphere. The reaction mixture was then stirred under a hydrogen atmosphere for 11 hours, filtered and concentrated in vacuo. The impure product was triturated with diethyl ether and filtered to give the title compound as a colourless solid (2 mg, 30%);

Workup

  1. filtrationfiltered
  2. concentrationconcentrated in vacuo
  3. customThe impure product was triturated with diethyl ether
  4. filtrationfiltered

Sources & evidence

ORD record
ord-58d018a5af37436eba400c9b90819f4f
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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