Methanol → HCID 59729278, compound

HRID 600469Notes

Reaction equation

HRID 600469 reaction equation
[N:1]1([C:6]2[C:7]3[NH:14][CH:13]=[C:12]([C:15]([O:17]CC)=[O:16])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1.O[Li].O.CO>C1COCC1.O>[N:1]1([C:6]2[C:7]3[NH:14][CH:13]=[C:12]([C:15]([OH:17])=[O:16])[C:8]=3[N:9]=[CH:10][N:11]=2)[CH:5]=[CH:4][CH:3]=[N:2]1

Participants

6

Reactant 3

HCID 887MethanolHCID 168937Lithium hydroxide, monohydrate2×HCID 59729280HCID 59729280, compound

Product 1

HCID 59729278HCID 59729278, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 4-(1H-pyrazol-1-yl)-5H-pyrrolo[3,2-d]pyrimidine-7-carboxylate 49 (2.0 g, 7.8 mmol) in THF (45 mL) was added a solution of LiOH.H2O (1.3 g, 31 mmol) in H2O (30 mL) and the reaction was stirred at 100° C. for 16 h. Additional LiOH.H2O (2.0 g, 48 mmol) was added, heating continued for 2 h, MeOH was added (10 mL) and heating continued at 100° C. for 1d. The reaction mixture was cooled, filtered, concentrated to ˜20% volume and neutralized with ice and conc HCl. The white precipitate that formed was collected by filtration and washed with brine, H2O, EtOAc, and Et2O to yield 50 (quantitative), which was used without further purification. 1H NMR: (500 MHz, DMSO-d6) δ 12.07 (br s, 1H), 8.89 (br s, 1H), 8.75 (s, 1H), 8.14 (s, 1H), 8.09 (br s, 1H), 6.76-6.73 (m, 1H);

Workup

  1. temperatureheating
  2. waitcontinued for 2 h
  3. temperatureheating
  4. temperatureThe reaction mixture was cooled
  5. filtrationfiltered
  6. concentrationconcentrated to ˜20% volume
  7. customThe white precipitate that formed
  8. filtrationwas collected by filtration
  9. washwashed with brine, H2O, EtOAc, and Et2O

Sources & evidence

ORD record
ord-49b851d9afb54446b89831630d547258
Source dataset
uspto-grants-2011_03
Patent number
US07902204B2

Reaction notes

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