Sodium Hydroxide → HCID 66590905, compound

HRID 1092285Notes

Reaction equation

HRID 1092285 reaction equation
[OH-].[Na+].[CH3:3][N:4]([C:13]1[CH:14]=[C:15]([C:19]2[CH:20]=[N:21][C:22]([CH:25]=[CH:26][C:27]([O-:29])=[O:28])=[N:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6]>O1CCCC1.O>[CH3:3][N:4]([C:13]1[CH:14]=[C:15]([C:19]2[CH:20]=[N:21][C:22]([CH:25]=[CH:26][C:27]([OH:29])=[O:28])=[N:23][CH:24]=2)[CH:16]=[CH:17][CH:18]=1)[C:5]([NH:7][CH2:8][CH2:9][CH2:10][CH2:11][CH3:12])=[O:6]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 86618121HCID 86618121, compound

Product 1

HCID 66590905HCID 66590905, compoundYield 22.1%

Reagents, catalysts & solvents 2

HCID 962WaterCatalystHCID 8028TetrahydrofuranSolvent

Procedure

10 mg (242.5 μmol, 2.5 eq) of sodium hydroxide pellets are added to a solution of 37.6 mg (97 μmol, 1 eq) of 3-{5-[3-(1-methyl-3-pentylureido)phenyl]pyrimidine-2-acrylate in 2 ml of tetrahydrofuran and 4 drops of water. The reaction mixture is stirred for 8 hours at room temperature. The reaction medium is concentrated and then diluted with 10 ml of water and washed with twice 10 ml of dichloromethane. The aqueous phase is acidified with 1 N hydrochloric acid and then extracted with ethyl acetate. The organic phases are combined and dried over sodium sulfate. The solvents are evaporated off and the residue is then chromatographed on a preparative silica plate (95/5/0.5% dichloromethane/methanol/aqueous ammonia). 7.9 mg of 3-{5-[3-(1-methyl-3-pentylureido)phenyl]pyrimidin-2-yl}acrylic acid are obtained in the form of beige-colored crystals. Yield=22%.

Workup

  1. concentrationThe reaction medium is concentrated
  2. additiondiluted with 10 ml of water
  3. washwashed with twice 10 ml of dichloromethane
  4. extractionextracted with ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. customThe solvents are evaporated off
  7. customthe residue is then chromatographed on a preparative silica plate (95/5/0.5% dichloromethane/methanol/aqueous ammonia)

Sources & evidence

ORD record
ord-1181527f8ec943a5b2d9202cc4a577af
Source dataset
uspto-grants-2012_03
Patent number
US08129416B2

Reaction notes

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