2-Chloropyrimidine-4-carbonitrile → HCID 21959645, compound

HRID 1924115Notes

Reaction equation

HRID 1924115 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[N:9])[CH:5]=[CH:4][N:3]=1.[C:10](OC([O-])=O)([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11]>CO.[Ni]>[C:13]([O:12][C:10](=[O:11])[NH:9][CH2:8][C:6]1[CH:5]=[CH:4][N:3]=[C:2]([Cl:1])[N:7]=1)([CH3:16])([CH3:15])[CH3:14]

Participants

5

Reactant 2

HCID 2466472-Chloropyrimidine-4-carbonitrileHCID 22064466Tert-butyldicarbonate

Product 1

HCID 21959645HCID 21959645, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 935NickelCatalystHCID 887MethanolSolvent

Procedure

2-Chloropyrimidine-4-carbonitrile (24 g), 40.8 g of t-butyl dicarbonate (Boc2O) in 1.2 L of methanol and 5 g of Raney nickel (Raney 2400) were charged in an autoclave. The autoclave was sealed and purged with hydrogen. The hydrogenation was run at 30 psi hydrogen gas. The reduction was carried out to completion and the reactor was vented and purged with nitrogen. The reaction mixture was filtered over diatomaceous earth and the filtrate was concentrated. The residue was purified by chromatography to yield the title compound (35 g, 84%) as white solid of melting point of 86-88° C.

Workup

  1. customThe autoclave was sealed
  2. custompurged with hydrogen
  3. custompurged with nitrogen
  4. filtrationThe reaction mixture was filtered over diatomaceous earth
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by chromatography

Sources & evidence

ORD record
ord-c365839b077a400bb5be74e6ab92efe5
Source dataset
uspto-grants-2012_05
Patent number
US08178540B2

Reaction notes

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