Lithium hydroxide, monohydrate → HCID 118863130, compound

HRID 63891Notes

Reaction equation

HRID 63891 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]([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)[S:18][C:12]=2[N:11]([CH3:35])[C:10]1=[O:36])=O.O[Li].O>C1COCC1.O.C(Cl)Cl>[OH:5][CH2:6][CH2:7][CH2:8][N:9]1[C:14](=[O:15])[C:13]2[C:16]([CH2:30][CH2:31][CH:32]([CH3:34])[CH3:33])=[C:17]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)[S:18][C:12]=2[N:11]([CH3:35])[C:10]1=[O:36]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 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-trifluoroacetate

Product 1

HCID 118863130HCID 118863130, compoundYield 51.6%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 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 (35 mg, 0.062 mmol) in THF (4 mL) and water (4 mL) was added LiOH.H2O (5.19 mg, 0.123 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 3-(3-hydroxypropyl)-5-isopentyl-1-methyl-6-(3-(trifluoromethoxy)phenyl)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (15 mg, 51.6% yield) as a white solid. 1H NMR (DMSO-d6) δ: 7.65 (t, J=8.0 Hz, 1H), 7.47 (dd, J=12.5, 8.3 Hz, 2H), 7.41 (s, 1H), 4.49 (s, 1H), 4.02-3.89 (m, 2H), 3.47 (s, 5H), 2.91-2.78 (m, 2H), 1.78-1.63 (m, 2H), 1.51 (dd, J=12.4 and 6.0 Hz, 1H), 1.48-1.37 (m, 2H), 0.81 (d, J=6.4 Hz, 6H). LCMS: MH+ 471 and TR=3.347 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-fcb5693ec601434eae57edc2fa5a6aac
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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