Lithium Hydroxide → HCID 58072960, compound

HRID 632907Notes

Reaction equation

HRID 632907 reaction equation
C[O:2][C:3](=[O:27])[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]([CH3:25])[N:13]=[CH:12][N:11]=2)=[CH:6][C:5]=1[Cl:26].[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:27])=[O:2])=[C:5]([Cl:26])[CH:6]=3)=[N:11][CH:12]=[N:13][C:14]=2[CH3:25])=[CH:23][CH:22]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58072999HCID 58072999, compound

Product 1

HCID 58072960HCID 58072960, 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 13.8 g (36.4 mmol) 4-[5-(6-amino-pyridin-3-ylethynyl)-6-methyl-pyrimidin-4-yl]-2-chloro-benzoic acid methyl ester using 7.64 g (182 mmol.) LiOH in 200 mL water and 400 mL THF. The reaction mixture is stirred over night at 50° C. 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 MeOH. After drying 12.1 g of the desired product is obtained, which is used for the next step without further purification.

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 MeOH
  5. dry with materialAfter drying 12.1 g of the desired product
  6. customis obtained
  7. customwhich is used for the next step without further purification

Sources & evidence

ORD record
ord-aad7d3babfb248298a0a35aea6026f30
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

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