Lithium Hydroxide → HCID 58072751, compound

HRID 632899Notes

Reaction equation

HRID 632899 reaction equation
C[O:2][C:3](=[O:29])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([C:16]#[C:17][C:18]3[C:19]([CH3:25])=[N:20][C:21]([NH2:24])=[CH:22][CH:23]=3)=[C:14]([CH2:26][CH3:27])[N:13]=[CH:12][N:11]=2)=[CH:6][C:5]=1[F:28].[Li+].[OH-]>O.C1COCC1>[NH2:24][C:21]1[N:20]=[C:19]([CH3:25])[C:18]([C:17]#[C:16][C:15]2[C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:29])=[O:2])=[C:5]([F:28])[CH:6]=3)=[N:11][CH:12]=[N:13][C:14]=2[CH2:26][CH3:27])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58072719HCID 58072719, compound

Product 1

HCID 58072751HCID 58072751, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

The title compound is synthesized according to general procedure GP8 starting from 4.0 g (10.3 mmol) 4-[5-(6-Amino-2-methyl-pyridin-3-ylethynyl)-6-ethyl-pyrimidin-4-yl]-2-fluoro-benzoic acid methyl ester using 1.29 g (30.7 mmol.) LiOH in 40 mL water and 200 mL THF. The reaction mixture is stirred over night at 50° C. The solvent is removed under reduced pressure and the residie is taken up in water. Aqueous 1 M HCl is added until pH 5 is reached. The precipitated product is filtered off and washed with ACN. After drying 1.3 g (32%) of the desired product are obtained a solid material.

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionAqueous 1 M HCl is added until pH 5
  3. filtrationThe precipitated product is filtered off
  4. washwashed with ACN
  5. dry with materialAfter drying 1.3 g (32%) of the desired product
  6. customare obtained a solid material

Sources & evidence

ORD record
ord-c81da39aa91f4d1c99ba72289793ce49
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

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