Hydrochloric Acid → 2-(4,6-Dimethoxypyrimidine-2-yl)-2-(3-methoxymethyl-2-nitrophenyl)acetonitrile

HRID 989602Notes

Reaction equation

HRID 989602 reaction equation
[H-].[Na+].[CH3:3][O:4][CH2:5][C:6]1[C:7]([N+:15]([O-:17])=[O:16])=[C:8]([CH2:12][C:13]#[N:14])[CH:9]=[CH:10][CH:11]=1.[H][H].[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24](S(C)(=O)=O)[N:23]=1.Cl.[CH2:35]([OH:37])[CH3:36]>CN(C)C=O>[CH:35]([O:37][CH:6]([CH3:11])[CH3:5])([CH3:20])[CH3:36].[CH3:20][O:21][C:22]1[CH:27]=[C:26]([O:28][CH3:29])[N:25]=[C:24]([CH:12]([C:8]2[CH:9]=[CH:10][CH:11]=[C:6]([CH2:5][O:4][CH3:3])[C:7]=2[N+:15]([O-:17])=[O:16])[C:13]#[N:14])[N:23]=1

Participants

9

Reactant 6

HCID 313Hydrochloric AcidHCID 702EthanolHCID 24758Sodium hydrideHCID 8383634,6-Dimethoxy-2-(methylsulfonyl)pyrimidineHCID 12090363(3-Methoxymethyl-2-nitro-phenyl)acetonitrileHCID 178418361HCID 178418361, compound

Product 2

HCID 7914Diisopropyl EtherHCID 120903622-(4,6-Dimethoxypyrimidine-2-yl)-2-(3-methoxymethyl-2-nitrophenyl)acetonitrileYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
10 °C

Procedure

11.2 g (0.28 M) of 60% sodium hydride was suspended in 100 ml of N,N-dimethylformamide. While the suspension was cooled to 10° C. or lower in an ice water bath and stirred, there-to was dropwise added a solution of 29 g (0.14 M) of 3-methoxymethyl-2-nitrophenylacetonitrile dissolved in 100 ml of N,N-dimethylformamide. After the completion of the dropwise addition, the mixture was stirred at room temperature until there was no evolution of hydrogen. While the mixture was cooled to 10° C. or lower in an ice water bath and stirred, thereto was added 30 g (0.14 M) of 4,6-dimethoxy-2-methylsulfonylpyrimidine. The mixture was stirred at room temperature for 12 hours. The reaction mixture was poured into ice water. The mixture was acidified with 10% hydrochloric acid. The resulting crude crystals were collected by filtration, washed with water and a mixed solvent of ethanol and isopropyl ether to obtain 42 g (yield: 87%) of 2-(4,6-dimethoxypyrimidine-2-yl)-2-(3-methoxymethyl-2-nitrophenyl)acetonitrile as a reddish brown powder (melting point: 112 to 113° C.).

Workup

  1. additionAfter the completion of the dropwise addition
  2. stirringthe mixture was stirred at room temperature until there
  3. temperatureWhile the mixture was cooled to 10° C. or lower in an ice water bath
  4. stirringstirred
  5. stirringThe mixture was stirred at room temperature for 12 hours
  6. filtrationThe resulting crude crystals were collected by filtration
  7. washwashed with water

Sources & evidence

ORD record
ord-743824831acb405fae8ad8d3f493bbff
Source dataset
uspto-grants-2002_10
Patent number
US06458748B1

Reaction notes

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