Lithium hydroxide, monohydrate → HCID 86712722, compound

HRID 1779084Notes

Reaction equation

HRID 1779084 reaction equation
O[Li].O.[CH3:4][C:5]1[C:6]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][C:27]([O:29]C)=[O:28])=[N:7][C:8]([NH:11][C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[N:9][CH:10]=1>O.C1COCC1>[CH3:4][C:5]1[C:6]([CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=2[CH2:26][C:27]([OH:29])=[O:28])=[N:7][C:8]([NH:11][C:12]2[CH:13]=[N:14][N:15]([CH3:17])[CH:16]=2)=[N:9][CH:10]=1

Participants

5

Reactant 2

HCID 168937Lithium hydroxide, monohydrateHCID 86712719HCID 86712719, compound

Product 1

HCID 86712722HCID 86712722, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

LiOH.H2O (0.534 g, 12.7 mmol) was added to a solution of methyl 2-(2-(2-(5-methyl-2-((1-methyl-1H-pyrazol-4-yl)amino)pyrimidin-4-yl)ethyl)phenyl)acetate (A116) (0.093 g, 0.25 mmol) in H2O (1 mL) and THF (10 mL) and the resulting mixture heated at 40° C. for 18 hours. The volatiles were removed in vacuo and the residue was diluted with EtOAc (100 mL), washed with aqueous 2 M HCl (50 mL), water (100 mL), brine (50 mL) and dried over MgSO4. The combined aqueous layers were additionally extracted with chloroform/isopropanol (4:1, 2×50 mL). The organic extracts were then combined, dried (Na2SO4), filtered and concentrated under reduced pressure to give the title compound A117 as a yellow solid (0.067 g, 75%); LCMS-A: rt 4.718 min; m/z 352 [M+H]+.

Workup

  1. customThe volatiles were removed in vacuo
  2. additionthe residue was diluted with EtOAc (100 mL)
  3. washwashed with aqueous 2 M HCl (50 mL), water (100 mL), brine (50 mL)
  4. dry with materialdried over MgSO4
  5. extractionThe combined aqueous layers were additionally extracted with chloroform/isopropanol (4:1, 2×50 mL)
  6. dry with materialdried (Na2SO4)
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-063ebb2ef2ba45c6b221e4c5e84e4600
Source dataset
uspto-grants-2016_02
Patent number
US09266864B2

Reaction notes

Loading…