Trifluoroacetic acid → 2-[1-Methyl-4-phenyl-2-(1,2,3,6-tetrahydropyridin-4-yl)-1H-imidazol-5-yl][1,3]thiazolo[5,4-d]pyrimidin-7-amine

HRID 32614Notes

Reaction equation

HRID 32614 reaction equation
[NH2:1][C:2]1[C:3]2[N:10]=[C:9]([C:11]3[N:15]([CH3:16])[C:14]([C:17]4[CH2:18][CH2:19][N:20](C(OC(C)(C)C)=O)[CH2:21][CH:22]=4)=[N:13][C:12]=3[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(O)(C(F)(F)F)=O>C(Cl)Cl>[CH3:16][N:15]1[C:11]([C:9]2[S:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH2:1])[C:3]=3[N:10]=2)=[C:12]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[N:13]=[C:14]1[C:17]1[CH2:18][CH2:19][NH:20][CH2:21][CH:22]=1

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 69553700tert-Butyl 4-[5-(7-amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1-methyl-4-phenyl-1H-imidazol-2-yl]-3,6-dihydropyridine-1(2H)-carboxylate

Product 1

HCID 104754582-[1-Methyl-4-phenyl-2-(1,2,3,6-tetrahydropyridin-4-yl)-1H-imidazol-5-yl][1,3]thiazolo[5,4-d]pyrimidin-7-amineYield 69.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

tert-Butyl 4-[5-(7-amino[1,3]thiazolo[5,4-d]pyrimidin-2-yl)-1-methyl-4-phenyl-1H-imidazol-2-yl]-3,6-dihydropyridine-1(2H)-carboxylate (Example 102) (20 mg) was dissolved in DCM (0.5 mL), TFA (2 mL) added, stirred at ambient temperature for 2 hours then concentrated in vacuo. The residue was diluted with saturated aqueous sodium bicarbonate, extracted with DCM (2×5 mL), organics dried, filtered and concentrated in vacuo. Purification by flash chromatography on silica gel eluting with 10% MeOH/DCM gave the title compound as a colourless solid (11 mg, 69%);

Workup

  1. concentrationthen concentrated in vacuo
  2. additionThe residue was diluted with saturated aqueous sodium bicarbonate
  3. extractionextracted with DCM (2×5 mL), organics dried
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customPurification by flash chromatography on silica gel eluting with 10% MeOH/DCM

Sources & evidence

ORD record
ord-a893fc653b684bd68c9222d92c12ecf9
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Reaction notes

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