Trifluoroacetic acid → 6-[1-(4-Aminobutyl)-4-phenyl-1H-imidazol-5-yl]-thieno[2,3-d]pyrimidin-4-amine

HRID 32644

Reaction equation

HRID 32644 reaction equation
[NH2:1][C:2]1[C:3]2[CH:10]=[C:9]([C:11]3[N:15]([CH2:16][CH2:17][CH2:18][CH2:19][NH:20]C(=O)OC(C)(C)C)[CH:14]=[N:13][C:12]=3[C:28]3[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=3)[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.C(O)(C(F)(F)F)=O.C([SiH](C(C)C)C(C)C)(C)C>O>[NH2:20][CH2:19][CH2:18][CH2:17][CH2:16][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[CH:10]=2)=[C:12]([C:28]2[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=2)[N:13]=[CH:14]1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 138754Silane, tris(1-methylethyl)-HCID 86760728tert-Butyl {4-[5-(4-aminothieno[2,3-d]pyrimidin-6-yl)-4-phenyl-1H-imidazol-1-yl]butyl}carbamate

Product 1

HCID 100216956-[1-(4-Aminobutyl)-4-phenyl-1H-imidazol-5-yl]-thieno[2,3-d]pyrimidin-4-amineYield 99.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

tert-Butyl {4-[5-(4-aminothieno[2,3-d]pyrimidin-6-yl)-4-phenyl-1H-imidazol-1-yl]butyl}carbamate (Example 173) (23 mg) was added to a mixture of TFA, water and triisopropyl silane (5:5:1) (5 ml) and stirred at ambient temperature for 1 hour. The reaction mixture was concentrated in vacuo and the residue purified by preparative RPHPLC (eluting with a gradient of MeCN and water containing 0.1% TFA) to give the title compound as a colourless solid (18 mg, 90%);

Workup

  1. concentrationThe reaction mixture was concentrated in vacuo
  2. customthe residue purified by preparative RPHPLC (
  3. washeluting with a gradient of MeCN and water containing 0.1% TFA)

Sources & evidence

ORD record
ord-0c1ae98f803a4acaa727d9ddea90ba00
Source dataset
uspto-grants-2008_09
Patent number
US07427616B2

Linked notes

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