Lithium Hydroxide → HCID 58073746, compound

HRID 1916189Notes

Reaction equation

HRID 1916189 reaction equation
C[O:2][C:3](=[O:27])[CH2:4][CH:5]1[CH2:10][CH2:9][N:8]([C:11]2[C:16]([C:17]#[C:18][C:19]3[CH:20]=[N:21][C:22]([NH2:25])=[CH:23][CH:24]=3)=[C:15]([CH3:26])[N:14]=[CH:13][N:12]=2)[CH2:7][CH2:6]1.[Li+].[OH-]>O.C1COCC1>[NH2:25][C:22]1[N:21]=[CH:20][C:19]([C:18]#[C:17][C:16]2[C:11]([N:8]3[CH2:9][CH2:10][CH:5]([CH2:4][C:3]([OH:27])=[O:2])[CH2:6][CH2:7]3)=[N:12][CH:13]=[N:14][C:15]=2[CH3:26])=[CH:24][CH:23]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 58073689HCID 58073689, compound

Product 1

HCID 58073746HCID 58073746, 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 2.87 g (7.85 mmol) {1-[5-(6-amino-pyridin-3-ylethynyl)-6-methyl-pyrimidin-4-yl]-piperidin-4-yl}-acetic acid methyl ester using 0.82 g (19.6 mmoL) LiOH in 10 mL water and 40 mL THF. The reaction mixture is stirred over night at 50° C. The THF is removed under reduced pressure and the residue is taken up DCM and MeOH and separated from insoluble material. The filtrate is dried over MgSO4 and the solvent is removed under reduced pressure. After drying 2.9 g (95%) of crude product is obtained which is used for the next step without purification.

Workup

  1. customThe THF is removed under reduced pressure
  2. customseparated from insoluble material
  3. dry with materialThe filtrate is dried over MgSO4
  4. customthe solvent is removed under reduced pressure
  5. dry with materialAfter drying 2.9 g (95%) of crude product
  6. customis obtained which
  7. customis used for the next step without purification

Sources & evidence

ORD record
ord-d53f08e20f534ac596531fb9772add4a
Source dataset
uspto-grants-2013_12
Patent number
US08618111B2

Reaction notes

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