Water → 6-{4-[6-(4-Fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl}-5-methyl-pyridine-2-carboxylic acid

HRID 2195065Notes

Reaction equation

HRID 2195065 reaction equation
C[O:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([N:12]2[CH2:17][CH2:16][N:15]([C:18]3[CH:23]=[C:22]([C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[N:21]=[C:20]([N:31]4[CH2:35][CH2:34][CH2:33][C@H:32]4[CH3:36])[N:19]=3)[C@H:14]([CH3:37])[CH2:13]2)[N:6]=1)=[O:4].O.O[Li].O>C1COCC1>[F:30][C:27]1[CH:26]=[CH:25][C:24]([C:22]2[N:21]=[C:20]([N:31]3[CH2:35][CH2:34][CH2:33][C@H:32]3[CH3:36])[N:19]=[C:18]([N:15]3[CH2:16][CH2:17][N:12]([C:7]4[N:6]=[C:5]([C:3]([OH:4])=[O:2])[CH:10]=[CH:9][C:8]=4[CH3:11])[CH2:13][C@H:14]3[CH3:37])[CH:23]=2)=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 962WaterHCID 168937Lithium hydroxide, monohydrateHCID 591683776-{4-[6-(4-Fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl}-5-methyl-pyridine-2-carboxylic acid methyl ester

Product 1

HCID 115622386-{4-[6-(4-Fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl}-5-methyl-pyridine-2-carboxylic acid

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 6-{4-[6-(4-fluoro-phenyl)-2-(2-(R)-methyl-pyrrolidin-1-yl)-pyrimidin-4-yl]-3-(R)-methyl-piperazin-1-yl}-5-methyl-pyridine-2-carboxylic acid methyl ester (300 mg, 0.595 mmol) in THF, add water dropwise until the cloudiness almost persists. To this mixture add LiOH.H2O (50 mg, 1.2 mmol). Heat the mixture at 50° C. for 2 h, and then concentrate under reduced pressure. Add a small amount of water to the residue. Adjust the final pH to 6 and collect the off-white solid via filtration. Wash the solid with water and dry to afford the title compound.

Workup

  1. concentrationconcentrate under reduced pressure
  2. additionAdd a small amount of water to the residue
  3. customcollect the off-white solid
  4. filtrationvia filtration
  5. washWash the solid with water
  6. customdry

Sources & evidence

ORD record
ord-9038900300594125b792b0c266e4cd9d
Source dataset
uspto-grants-2012_12
Patent number
US08334382B2

Reaction notes

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