Lithium hydroxide, monohydrate → HCID 118863780, compound

HRID 60345Notes

Reaction equation

HRID 60345 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH2:30][C:31]3[CH:36]=[CH:35][C:34]([Cl:37])=[CH:33][CH:32]=3)[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]([CH3:38])[C:9]1=[O:39])(=O)C.O[Li].O>C1COCC1.O.C(Cl)Cl>[Cl:37][C:34]1[CH:35]=[CH:36][C:31]([CH2:30][N:15]2[C:12]3[C:13](=[O:14])[N:8]([CH2:7][CH2:6][CH2:5][OH:4])[C:9](=[O:39])[N:10]([CH3:38])[C:11]=3[C:17]([CH3:18])=[C:16]2[C:19]2[CH:24]=[CH:23][CH:22]=[C:21]([O:25][C:26]([F:27])([F:28])[F:29])[CH:20]=2)=[CH:32][CH:33]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118863785HCID 118863785, compound

Product 1

HCID 118863780HCID 118863780, compoundYield 27%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(5-(4-chlorobenzyl)-1,7-dimethyl-2,4-dioxo-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (120 mg, 0.212 mmol) in THF (5 mL) and water (5 mL) was added LiOH.H2O (17.9 mg, 0.425 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 5-(4-chlorobenzyl)-3-(3-hydroxypropyl)-1,7-dimethyl-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidine-2,4 (3H,5H)-dione (15 mg, 27% yield) as a white solid. 1H NMR (CDCl3) δ: 7.49 (t, J=8.0 Hz, 1H), 7.32 (d, J=8.3 Hz, 1H), 7.13 (dd, J=16.3, 8.0 Hz, 3H), 7.04 (s, 1H), 6.71 (d, J=8.4 Hz, 2H), 5.46 (s, 2H), 4.31-4.15 (m, 2H), 3.74 (s, 3H), 3.65 (s, 1H), 3.50 (s, 2H), 2.20 (s, 3H), 1.98-1.81 (m, 2H). LCMS: MH+ 522 and TR=3.111 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-60f0f3a96a36442184c911164ce1adf1
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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