Trifluoroacetic acid → HCID 118863116, compound

HRID 63888Notes

Reaction equation

HRID 63888 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:37]=[CH:38][CH:39]=1)[O:5][C:6]1[S:27][C:9]2[N:10]([CH3:26])[C:11](=[O:25])[N:12]([CH2:15][CH2:16][CH2:17]OC3CCCCO3)[C:13](=[O:14])[C:8]=2[C:7]=1[CH:28]([C:30]1[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=1)O.[SiH](CC)(CC)CC.[C:47]([OH:53])([C:49]([F:52])([F:51])[F:50])=[O:48]>CC(=O)OCC.O>[F:50][C:49]([F:52])([F:51])[C:47]([O:53][CH2:17][CH2:16][CH2:15][N:12]1[C:13](=[O:14])[C:8]2[C:7]([CH2:28][C:30]3[CH:31]=[CH:32][C:33]([Cl:36])=[CH:34][CH:35]=3)=[C:6]([O:5][C:4]3[CH:37]=[CH:38][CH:39]=[C:2]([Cl:1])[CH:3]=3)[S:27][C:9]=2[N:10]([CH3:26])[C:11]1=[O:25])=[O:48]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 1188631066-(3-chlorophenoxy)-5-((4-chlorophenyl) (hydroxy)methyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione

Product 1

HCID 118863116HCID 118863116, compoundYield 89.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(3-chlorophenoxy)-5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-(tetrahydro-2H-pyran-2-yloxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (45 mg, 0.076 mmol) in TFA (0.9 mL) was added Et3SiH (0.3 mL). The reaction was stirred at RT for 15 min then diluted with EA (20 mL) and water (20 mL). The organic layer was dried over Na2SO4 and concentrated to give 3-(5-(4-chlorobenzyl)-6-(3-chlorophenoxy)-1-methyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propyl 2,2,2-trifluoroacetate (40 mg, 89.5% yield) as an oil. LCMS: MH+ 587 and TR=2.308 min.

Workup

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

Sources & evidence

ORD record
ord-75759bcf99af49c1be0699cb64c8d3cc
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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