Lithium hydroxide, monohydrate → HCID 118863146, compound

HRID 63908Notes

Reaction equation

HRID 63908 reaction equation
FC(F)(F)C([O:5][CH2:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[C:13]2[C:16]([CH2:26][C:27]3[CH:32]=[CH:31][C:30]([Cl:33])=[CH:29][CH:28]=3)=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=3)[S:18][C:12]=2[N:11]([CH3:34])[C:10]1=[O:35])=O.O[Li].O>C1COCC1.O.C(Cl)Cl>[Cl:33][C:30]1[CH:29]=[CH:28][C:27]([CH2:26][C:16]2[C:13]3[C:14](=[O:15])[N:9]([CH2:8][CH2:7][CH2:6][OH:5])[C:10](=[O:35])[N:11]([CH3:34])[C:12]=3[S:18][C:17]=2[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([Cl:25])[CH:20]=2)=[CH:32][CH:31]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 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-trifluoroacetate

Product 1

HCID 118863146HCID 118863146, compoundYield 48.1%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-(4-chlorobenzyl)-6-(3-chlorophenyl)-1-methyl-2,4-dioxo-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propyl 2,2,2-trifluoroacetate (40 mg, 0.070 mmol) in THF (4 mL) and water (4 mL) was added LiOH.H2O (5.88 mg, 0.14 mmol). The reaction was stirred at RT for 15 min then diluted with DCM (5 mL) and water (5 mL). The organic layer was dried over Na2SO4 and concentrated to a residue which was purified by Prep HPLC to give 5-(4-chlorobenzyl)-6-(3-chlorophenyl)-3-(3-hydroxypropyl)-1-methylthieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (16 mg, 48.1% yield) as a white solid. 1H-NMR (DMSO-d6) δ: 7.49 (d, J=5.1 Hz, 2H), 7.40 (s, 1H), 7.36-7.32 (m, 1H), 7.29 (d, J=8.4 Hz, 2H), 7.04 (d, J=8.4 Hz, 2H), 4.45 (t, J=5.2 Hz, 1H), 4.30 (s, 2H), 3.97-3.82 (m, 2H), 3.52 (d, J=14.8 Hz, 3H), 3.42 (dd, J=11.7, 6.3 Hz, 2H), 1.67 (dd, J=14.2, 6.9 Hz, 2H). LCMS: MH+ 475 and TR=3.252 min.

Workup

  1. dry with materialThe organic layer was dried over Na2SO4
  2. concentrationconcentrated to a residue which
  3. customwas purified by Prep HPLC

Sources & evidence

ORD record
ord-09e73de851c142ce8219225138f84e54
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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