Trifluoroacetic acid → 3-(5-isopentyl-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydro thieno[2,3-d]pyrimidin-3(4H)-yl)propyl 2,2,2-trifluoroacetate

HRID 63890Notes

Reaction equation

HRID 63890 reaction equation
O[CH:2]([C:7]1[C:15]2[C:14](=[O:16])[N:13]([CH2:17][CH2:18][CH2:19]OC3CCCCO3)[C:12](=[O:27])[N:11]([CH3:28])[C:10]=2[S:9][C:8]=1[C:29]1[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]([F:39])([F:38])[F:37])[CH:30]=1)[CH2:3][CH:4]([CH3:6])[CH3:5].C([SiH](CC)CC)C.[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48]>C(Cl)Cl.O>[F:50][C:49]([F:52])([F:51])[C:47]([O:53][CH2:19][CH2:18][CH2:17][N:13]1[C:14](=[O:16])[C:15]2[C:7]([CH2:2][CH2:3][CH:4]([CH3:5])[CH3:6])=[C:8]([C:29]3[CH:34]=[CH:33][CH:32]=[C:31]([O:35][C:36]([F:38])([F:39])[F:37])[CH:30]=3)[S:9][C:10]=2[N:11]([CH3:28])[C:12]1=[O:27])=[O:48]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 1188631145-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy) propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione2×

Product 1

HCID 1188630923-(5-isopentyl-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydro thieno[2,3-d]pyrimidin-3(4H)-yl)propyl 2,2,2-trifluoroacetateYield 88.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 5-(1-hydroxy-3-methylbutyl)-1-methyl-3-(3-((tetrahydro-2H-pyran-2-yl)oxy) propyl)-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (See Compound 22, Step 3, 40 mg, 0.070 mmol) in TFA (2 mL) was added triethylsilane (1 mL). The reaction was stirred at RT for 48 h then diluted with DCM (5 mL) and water (5 mL). The organic layer was dried over Na2SO4 and concentrated to give 3-(5-isopentyl-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1,2-dihydrothieno[2,3-d]pyrimidin-3 (4H)-yl)propyl 2,2,2-trifluoroacetate (35 mg, 88.1% yield) as an oil. LCMS: MH+ 567 and TR=2.383 min.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated

Sources & evidence

ORD record
ord-84cbf35e1d924ed88087c31c6471bc79
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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