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

HRID 60361Notes

Reaction equation

HRID 60361 reaction equation
C([O:4][CH2:5][CH2:6][CH2:7][N:8]1[C:13](=[O:14])[C:12]2[N:15]([CH2:29][C:30]3[CH:35]=[CH:34][C:33]([Cl:36])=[CH:32][CH:31]=3)[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]([CH3:37])[C:9]1=[O:38])(=O)C.O[Li].O>C1COCC1.O.C(Cl)Cl>[Cl:36][C:33]1[CH:34]=[CH:35][C:30]([CH2:29][N:15]2[C:12]3[C:13](=[O:14])[N:8]([CH2:7][CH2:6][CH2:5][OH:4])[C:9](=[O:38])[N:10]([CH3:37])[C:11]=3[CH:17]=[C:16]2[C:18]2[CH:23]=[CH:22][CH:21]=[C:20]([O:24][C:25]([F:26])([F:27])[F:28])[CH:19]=2)=[CH:31][CH:32]=1

Participants

6

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 118871741HCID 118871741, compound

Product 1

HCID 1188637675-[(4-Chlorophenyl)methyl]-3-(3-hydroxypropyl)-1-methyl-6-[3-(trifluoromethoxy)phenyl]pyrrolo[3,2-d]pyrimidine-2,4-dioneYield 14.6%

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)phenyl)-1H-pyrrolo[3,2-d]pyrimidin-3(2H,4H,5H)-yl)propyl acetate (30 mg, 0.054 mmol) in THF (5 mL) and water (5 mL) was added LiOH.H2O (4.58 mg, 0.109 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-methyl-6-(3-(trifluoromethoxy)phenyl)-1H-pyrrolo[3,2-d]pyrimidine-2,4 (3H,5H)-dione (4 mg, 14.4% yield) as a white solid. 1H NMR (CDCl3) δ: 7.47 (t, J=8.0 Hz, 1H), 7.31 (d, J=8.6 Hz, 1H), 7.26-7.24 (m, 1H), 7.20 (d, J=8.3 Hz, 3H), 6.81 (d, J=8.4 Hz, 2H), 6.10 (s, 1H), 5.59 (s, 2H), 4.26-4.13 (m, 2H), 3.56 (d, J=6.7 Hz, 1H), 3.50 (d, J=9.8 Hz, 5H), 1.90 (d, J=5.4 Hz, 2H). LCMS: MH+ 508 and TR=3.007 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-f4de0f1736894752abece72f40e608af
Source dataset
uspto-grants-2016_09
Patent number
US09440983B2

Reaction notes

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