Hydrochloric Acid → US9290457, Intermediate 6

HRID 927002Notes

Reaction equation

HRID 927002 reaction equation
C[O:2][C:3](=[O:34])[C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][C:5]=1[CH:12]1[C:17]([C:18](=[O:20])[CH3:19])=[C:16]([CH3:21])[N:15]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[C:14](=[O:32])[N:13]1[CH3:33].[OH-].[Li+].O.Cl>O1CCOCC1>[C:18]([C:17]1[CH:12]([C:5]2[CH:6]=[CH:7][C:8]([C:10]#[N:11])=[CH:9][C:4]=2[C:3]([OH:34])=[O:2])[N:13]([CH3:33])[C:14](=[O:32])[N:15]([C:22]2[CH:27]=[CH:26][CH:25]=[C:24]([C:28]([F:31])([F:30])[F:29])[CH:23]=2)[C:16]=1[CH3:21])(=[O:20])[CH3:19]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 3939Lithium HydroxideHCID 118691667US9290457, Intermediate 52×

Product 1

HCID 118691679US9290457, Intermediate 6

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

2-[5-Acetyl-3,6-dimethyl-2-oxo-1-(3-trifluoromethyl-phenyl)-1,2,3,4-tetrahydro-pyrimidin-4-yl]-5-cyano-benzoic acid methyl ester (intermediate 5)(612 mg, 1.30 mmol) and lithium hydroxide (93.3 mg, 3.90 mmol) are stirred in 1,4-dioxane (12.0 ml) and water (6.0 mL) at room temperature for 20 min Water (200 mL) is added and the mixture is acidified with hydrochloric acid (1.0 M, 44 mL) to a pH value of 3. The aqueous phase is extracted with ethyl acetate. The organic phase is washed twice with water, dried over MgSO4 and concentrated. Yield: 665 mg. ESI mass spectrum: [M+H]+=472; Retention time HPLC: 1.09 min (HPLC method Z018_S04).

Workup

  1. extractionThe aqueous phase is extracted with ethyl acetate
  2. washThe organic phase is washed twice with water
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. custom1.09 min (HPLC method Z018_S04)

Sources & evidence

ORD record
ord-fb2496847bf545878182e26885716edb
Source dataset
uspto-grants-2016_03
Patent number
US09290457B2

Reaction notes

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