Lithium hydroxide, monohydrate → HCID 118863118, compound

HRID 63882Notes

Reaction equation

HRID 63882 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]([CH2:31][C:32]3[CH:37]=[CH:36][C:35]([Cl:38])=[CH:34][CH:33]=3)=[C:17]([O:19][C:20]3[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:30])([F:29])[F:28])[CH:21]=3)[S:18][C:12]=2[N:11]([CH3:39])[C:10]1=[O:40])=O.[Li+].[OH-].O>C1COCC1.O.C(Cl)Cl>[Cl:38][C:35]1[CH:36]=[CH:37][C:32]([CH2:31][C:16]2[C:13]3[C:14](=[O:15])[N:9]([CH2:8][CH2:7][CH2:6][OH:5])[C:10](=[O:40])[N:11]([CH3:39])[C:12]=3[S:18][C:17]=2[O:19][C:20]2[CH:25]=[CH:24][CH:23]=[C:22]([O:26][C:27]([F:28])([F:29])[F:30])[CH:21]=2)=[CH:33][CH:34]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118863088HCID 118863088, compound

Product 1

HCID 118863118HCID 118863118, compoundYield 47.4%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-(4-chlorobenzyl)-1-methyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenoxy)-1,2-dihydrothieno[2,3-d]pyrimidin-3(4H)-yl)propyl 2,2,2-trifluoroacetate (25 mg, 0.039 mmol) in THF (4 mL) and water (4 mL) was added LiOH/H2O (3.29 mg, 0.079 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)-3-(3-hydroxypropyl)-1-methyl-6-(3-(trifluoromethoxy)phenoxy)thieno[2,3-d]pyrimidine-2,4(1H,3H)-dione (10 mg, 47.1% yield) as a white solid. 1H NMR (DMSO-d6) δ: 7.49 (t, J=8.3 Hz, 1H), 7.21 (dd, J=18.8, 8.6 Hz, 4H), 7.17-7.07 (m, 2H), 7.03 (s, 1H), 4.50 (t, J=5.1 Hz, 1H), 4.10 (s, 2H), 3.99-3.86 (m, 2H), 3.51-3.42 (m, 2H), 3.41 (s, 3H), 1.69 (s, 2H). LCMS: MH+ 541 and TR=3.317 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-4e16f2138fe44614aae50e1e086b0bb2
Source dataset
uspto-grants-2016_09
Patent number
US09447114B2

Reaction notes

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