Sodium → HCID 59351601, compound

HRID 1889421Notes

Reaction equation

HRID 1889421 reaction equation
Cl[C:2]1[N:7]([CH2:8][C:9]2[CH:14]=[CH:13][C:12]([C:15]3[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=3)=[CH:11][CH:10]=2)[C:6](=[O:23])[NH:5][C:4](=[O:24])[CH:3]=1.[Na]>C(O)CC>[O:23]=[C:6]1[NH:5][C:4](=[O:24])[CH:3]=[C:2]([O:24][CH2:4][CH2:3][CH3:2])[N:7]1[CH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([C:21]#[N:22])=[CH:17][CH:18]=[CH:19][CH:20]=2)=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 5360545SodiumHCID 59351773HCID 59351773, compound

Product 1

HCID 59351601HCID 59351601, compoundYield 95.1%

Reagents, catalysts & solvents 1

HCID 10311-PropanolSolvent2×

Conditions

Temperature
100 °C

Procedure

To a mixture of 4′-[(6-chloro-2,4-dioxo-3,4-dihydropyrimidin-1(2H)-yl)methyl]biphenyl-2-carbonitrile (2.3 g) and n-propanol (70 mL) was added a solution of sodium (0.24 g) in n-propanol (10 mL), and the mixture was stirred at 100° C. for 4 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was dissolved in water (100 mL). 1N Hydrochloric acid was added to adjust to pH 4, and the precipitated solid was recrystallized from methanol to give the title compound as colorless crystals (1.17 g, 47%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. dissolutionthe obtained residue was dissolved in water (100 mL)
  3. addition1N Hydrochloric acid was added
  4. customthe precipitated solid was recrystallized from methanol

Sources & evidence

ORD record
ord-ef0a85bc8bfd427ab380c704dec0384b
Source dataset
uspto-grants-2013_08
Patent number
US08501750B2

Reaction notes

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