Lithium Hydroxide → HCID 58072955, compound

HRID 632901Notes

Reaction equation

HRID 632901 reaction equation
C[O:2][C:3](=[O:28])[C:4]1[CH:9]=[CH:8][C:7]([C:10]2[C:15]([C:16]#[C:17][C:18]3[CH:19]=[N:20][C:21]([NH2:24])=[CH:22][CH:23]=3)=[C:14]([CH2:25][CH3:26])[N:13]=[CH:12][N:11]=2)=[CH:6][C:5]=1[F:27].[Li+].[OH-]>O.C1COCC1>[NH2:24][C:21]1[N:20]=[CH:19][C:18]([C:17]#[C:16][C:15]2[C:10]([C:7]3[CH:8]=[CH:9][C:4]([C:3]([OH:28])=[O:2])=[C:5]([F:27])[CH:6]=3)=[N:11][CH:12]=[N:13][C:14]=2[CH2:25][CH3:26])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58072881HCID 58072881, compound

Product 1

HCID 58072955HCID 58072955, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound is synthesized according to general procedure GP8 starting from 17.8 g (47.3 mmol) 4-[5-(6-amino-pyridin-3-ylethynyl)-6-ethyl-pyrimidin-4-yl]-2-fluoro-benzoic acid methyl ester using 3.97 g (94.6 mmol.) LiOH in 30 mL water and 300 mL THF. The reaction mixture is stirred over night at RT. 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 17.1 g (85%) 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 17.1 g (85%) of the desired product
  6. customare obtained a solid material

Sources & evidence

ORD record
ord-55c9e4eea47d45a88404619a39981c3d
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

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