Acetonitrile → HCID 15028930, compound

HRID 1091066Notes

Reaction equation

HRID 1091066 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][NH:9][C:10]2[N:11]([CH3:20])[CH2:12][N:13]([CH3:19])[CH2:14][C:15]=2[N+:16]([O-:18])=[O:17])=[CH:4][CH:3]=1.C(#N)C.[H-].[Na+].[C:26](OC=O)(=[O:28])C>C1COCC1>[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][N:9]([C:10]2[N:11]([CH3:20])[CH2:12][N:13]([CH3:19])[CH2:14][C:15]=2[N+:16]([O-:18])=[O:17])[CH:26]=[O:28])=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24758Sodium hydrideHCID 75269Acetic-formic anhydrideHCID 15676852HCID 15676852, compound

Product 1

HCID 15028930HCID 15028930, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a mixture of 0.27 g of 4-(6-chloro-3-pyridylmethylamino)-1,3-dimethyl-5-nitro-1,2,3,6-tetrahydropyrimidine (Compound No. 13), 5 ml of dry THF and 5 ml of dry acetonitrile was added 0.0239 g of sodium hydride (60%, in oil) in small portions over 1 minute with ice cooling. After the mixture was stirred at room temperature for 30 minutes, a solution of 0.24 g of formic acetic anhydride in 1 ml of THF was added dropwise over a period of 4 minutes with ice cooling and the mixture was then stirred at room temperature for 3 hours. The reaction mixture was concentrated and purified by column chromatography (eluent: dichloromethane-methanol (20:1)) to give 0.14 g of 4-[N-(6-chloro-3-pyridylmethyl)-N-formylamino]-1,3-dimethyl-5-nitro-1,2,3,6-tetrahydropyrimidine (Compound No. 30) as a syrup.

Workup

  1. stirringthe mixture was then stirred at room temperature for 3 hours
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by column chromatography (eluent: dichloromethane-methanol (20:1))

Sources & evidence

ORD record
ord-e67bf2ebcb1f44f782036892d11b46d8
Source dataset
uspto-grants-1992_01
Patent number
US05084459

Reaction notes

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