Lithium hydroxide, monohydrate → 3-(3-Hydroxypropyl)-1,5-dimethyl-6-[3-(trifluoromethoxy)phenyl]pyrrolo[3,2-d]pyrimidine-2,4-dione

HRID 60350Notes

Reaction equation

HRID 60350 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH3:29])[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=3)=[CH:17][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[N:15]([CH3:29])[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:28])([F:27])[F:26])[CH:19]=3)=[CH:17][C:11]=2[N:10]([CH3:30])[C:9]1=[O:31]

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118863774HCID 118863774, compound

Product 1

HCID 1188717423-(3-Hydroxypropyl)-1,5-dimethyl-6-[3-(trifluoromethoxy)phenyl]pyrrolo[3,2-d]pyrimidine-2,4-dioneYield 37%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(1,5-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (30 mg, 0.068 mmol) in THF (5 mL) and water (5 mL) was added LiOH.H2O (5.73 mg, 0.136 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)-1,5-dimethyl-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidine-2,4(3H,5H)-dione (10 mg, 36.9% yield) as a white solid. 1H NMR (CDCl3) δ: 7.54 (t, J=7.9 Hz, 1H), 7.38 (d, J=7.8 Hz, 1H), 7.32 (d, J=11.0 Hz, 2H), 6.03 (s, 1H), 4.29-4.17 (m, 2H), 3.98 (s, 3H), 3.72 (s, 1H), 3.54 (t, J=5.1 Hz, 2H), 3.50 (s, 3H), 1.99-1.84 (m, 2H). LCMS: MH+ 398 and TR=2.507 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-933e65a0d2e241e18eebc2e8bd25c8b3
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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