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

HRID 63907Notes

Reaction equation

HRID 63907 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[S:29][C:11]3[N:12]([CH3:28])[C:13](=[O:27])[N:14]([CH2:17][CH2:18][CH2:19]OC4CCCCO4)[C:15](=[O:16])[C:10]=3[C:9]=2[CH:30]([C:32]2[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=2)O)[CH:5]=[CH:6][CH:7]=1.C([SiH](CC)CC)C.[C:46]([OH:52])([C:48]([F:51])([F:50])[F:49])=[O:47]>C(Cl)Cl.O>[F:49][C:48]([F:51])([F:50])[C:46]([O:52][CH2:19][CH2:18][CH2:17][N:14]1[C:15](=[O:16])[C:10]2[C:9]([CH2:30][C:32]3[CH:33]=[CH:34][C:35]([Cl:38])=[CH:36][CH:37]=3)=[C:8]([C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([Cl:1])[CH:3]=3)[S:29][C:11]=2[N:12]([CH3:28])[C:13]1=[O:27])=[O:47]

Participants

6

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 118863133HCID 118863133, compound2×

Product 1

HCID 1188630873-(5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydro thieno[2,3-d]pyrimidin-3(4H)-yl)propyl 2,2,2-trifluoroacetateYield 80.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 6-(3-chlorophenyl)-5-((4-chlorophenyl)(hydroxy)methyl)-1-methyl-3-(3-((tetra hydro-2H-pyran-2-yl)oxy)propyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (See Compound 4, Step 2, 50 mg, 0.078 mmol) in TFA (1 mL) was added triethylsilane (0.5 mL). The reaction was stirred at RT for 2 h then diluted with DCM (5 mL) and water (5 mL). The organic layer was dried over Na2SO4 and concentrated to give 3-(5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydro thieno[2,3-d]pyrimidin-3(4H)-yl)propyl 2,2,2-trifluoroacetate (40 mg, 80.5% yield) as an oil. LCMS: MH+ 571 and TR=2.327 min. Used without further purification.

Workup

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

Sources & evidence

ORD record
ord-e8bcd5ea5e0c41fa8b66354b030b2aea
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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