Lithium Hydroxide → HCID 67176532, compound

HRID 1480002Notes

Reaction equation

HRID 1480002 reaction equation
[CH2:1]([C:8]1[N:13]=[N:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[C:23]([C:30]([O:32]C)=[O:31])=[CH:22][N:21]=3)[C@H:16]([CH3:34])[CH2:15]2)=[C:10]([CH3:35])[C:9]=1[CH3:36])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[Li+].[OH-]>C1COCC1.CCOC(C)=O>[CH2:1]([C:8]1[N:13]=[N:12][C:11]([N:14]2[CH2:19][CH2:18][N:17]([C:20]3[N:25]=[C:24]([C:26]([F:29])([F:28])[F:27])[C:23]([C:30]([OH:32])=[O:31])=[CH:22][N:21]=3)[C@H:16]([CH3:34])[CH2:15]2)=[C:10]([CH3:35])[C:9]=1[CH3:36])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 2

HCID 3939Lithium HydroxideHCID 59191593HCID 59191593, compound

Product 1

HCID 67176532HCID 67176532, compoundYield 96.6%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
75 °C

Procedure

To a solution of methyl 2-[(R)-4-(6-benzyl-4,5-dimethyl-pyridazin-3-yl)-2-methyl-piperazin-1-yl]-4-trifluoromethyl-pyrimidine-5-carboxylate (500 mg, 1.0 mmol, 1.0 eq) in THF (5 mL) is added an aqueous solution of LiOH (1 M, 2.0 mL, 2.0 mmol, 2.0 eq) and the resulting solution is heated to 75° C. for 4 h. The reaction mixture is diluted with EtOAc (50 mL) and washed with water (3×15 mL). The combined aqueous washes were adjusted to pH 6 with aqueous HCl (1 M), then extracted with dichloromethane (3×50 mL). The combined organic layers are dried over sodium sulfate and concentrated under reduced pressure to yield the desired product as a white solid (470 mg, 96%).

Workup

  1. washwashed with water (3×15 mL)
  2. extractionextracted with dichloromethane (3×50 mL)
  3. dry with materialThe combined organic layers are dried over sodium sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-c49bc872840f46bebd204094d4eca5d8
Source dataset
uspto-grants-2016_08
Patent number
US09409871B2

Reaction notes

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