Trifluoroacetic acid → HCID 178431873, compound

HRID 606382Notes

Reaction equation

HRID 606382 reaction equation
[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH2:23][CH2:24][S:25][C:26]4[N:30]=[CH:29][N:28](C(C5C=CC=CC=5)(C5C=CC=CC=5)C5C=CC=CC=5)[N:27]=4)[CH:17]=3)=[O:13])=[N:6][C:5]=2[S:4][CH:3]=1.C([SiH](CC)CC)C.FC(F)(F)C(O)=O>ClCCl>[CH3:1][C:2]1[C:10]2[C:9](=[O:11])[NH:8][C:7]([C:12]([NH:14][CH2:15][C:16]3[CH:21]=[CH:20][N:19]=[C:18]([O:22][CH2:23][CH2:24][S:25][C:26]4[N:30]=[CH:29][NH:28][N:27]=4)[CH:17]=3)=[O:13])=[N:6][C:5]=2[S:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 667689495-methyl-4-oxo-N-({2-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}ethyl)oxy]pyridin-4-yl}methyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide

Product 1

HCID 178431873HCID 178431873, compoundYield 21%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 5-methyl-4-oxo-N-({2-[(2-{[1-(triphenylmethyl)-1H-1,2,4-triazol-3-yl]thio}ethyl)oxy]pyridin-4-yl}methyl)-3,4-dihydrothieno[2,3-d]pyrimidine-2-carboxamide (395.0 mg, 0.576 mmol), triethylsilane (0.097 mL, 0.605 mmol) and trifluoroacetic acid (3.0 mL) in dichloromethane (10 mL) was stirred at room temperature for 2 hr. The reaction mixture was concentrated under reduced pressure, and the residue was crystallized from ethyl acetate-IPE to give the title compound as a white powder (53.6 mg, 21%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was crystallized from ethyl acetate-IPE

Sources & evidence

ORD record
ord-1cecab5a70094fe5ae92ab7637f7fba1
Source dataset
uspto-grants-2011_03
Patent number
US07915267B2

Reaction notes

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