Lithium hydroxide, monohydrate → HCID 118871740, compound

HRID 60364Notes

Reaction equation

HRID 60364 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[NH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)=[C:17]([CH3:18])[C:11]=2[N:10]([CH3:30])[C:9]1=[O:31])(=O)C.O[Li].O>C1COCC1.O.C(Cl)Cl>[OH:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[NH:15][C:16]([C:19]3[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:29])([F:28])[F:27])[CH:20]=3)=[C:17]([CH3:18])[C:11]=2[N:10]([CH3:30])[C:9]1=[O:31]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118863788HCID 118863788, compound

Product 1

HCID 118871740HCID 118871740, compoundYield 27.7%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1,7-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (40 mg, 0.091 mmol) in THF (5 mL) and water (5 mL) was added LiOH.H2O (7.64 mg, 0.182 mmol). The reaction was stirred at RT for 30 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)-1,7-dimethyl-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (10 mg, 27.6% yield) as a white solid. 1H NMR (CDCl3) δ: 9.58 (s, 1H), 7.54 (t, J=7.9 Hz, 1H), 7.42 (d, J=7.8 Hz, 1H), 7.31 (d, J=9.9 Hz, 2H), 4.30-4.09 (m, 2H), 3.76 (s, 3H), 3.64 (t, J=7.1 Hz, 1H), 3.56-3.41 (m, 2H), 2.42 (s, 3H), 1.92-1.74 (m, 2H). LCMS: MH+ 398 and TR=2.418 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-5affe3ea07444dc89fb7119295bf2020
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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