Lithium Hydroxide → HCID 58072586, compound

HRID 632912Notes

Reaction equation

HRID 632912 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[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[O:27][CH3:28].[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:29])=[O:2])=[C:5]([O:27][CH3:28])[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 58072584HCID 58072584, compound

Product 1

HCID 58072586HCID 58072586, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

The title compound is synthesized according to general procedure GP8 starting from 7.5 g (19.3 mmol) 4-[5-(6-amino-pyridin-3-ylethynyl)-6-ethyl-pyrimidin-4-yl]-2-methoxy-benzoic acid methyl ester using 4.05 g (96.5 mmol.) LiOH in 100 mL water and 200 mL THF. The reaction mixture is stirred over night at room temperature. The solvent is removed under reduced pressure and the residue is taken up in water. Aqueous 1 M HCl is added until pH 5-6 is reached. The precipitated product is filtered off and washed with water and Acetonitrile. After drying 6.5 g (89%) of the desired product is obtained as solid material.

Workup

  1. customThe solvent is removed under reduced pressure
  2. additionAqueous 1 M HCl is added until pH 5-6
  3. filtrationThe precipitated product is filtered off
  4. washwashed with water and Acetonitrile
  5. dry with materialAfter drying 6.5 g (89%) of the desired product
  6. customis obtained as solid material

Sources & evidence

ORD record
ord-74ca52a400ed462bbf1b8921f1dcfbfc
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

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