Lithium Hydroxide → HCID 58072943, compound

HRID 632908Notes

Reaction equation

HRID 632908 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[F: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]([F: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 58073015HCID 58073015, compound

Product 1

HCID 58072943HCID 58072943, 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 2.28 g (6.29 mmol) 4-[5-(6-amino-pyridin-3-ylethynyl)-6-methyl-pyrimidin-4-yl]-2-fluoro benzoic acid methyl ester using 1.32 g (31.5 mmol.) LiOH in 5 mL water and 50 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 is reached. The precipitated product is filtered off and taken up in water. After freeze drying 2.7 g of crude 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
  3. filtrationThe precipitated product is filtered off
  4. dry with materialAfter freeze drying 2.7 g of crude product
  5. customis obtained which
  6. customis used for the next step without further purification

Sources & evidence

ORD record
ord-34537c9f70b94370963515dae063754c
Source dataset
uspto-grants-2016_04
Patent number
US09321771B2

Reaction notes

Loading…