Dimethylformamide → HCID 59823351, compound

HRID 1801725Notes

Reaction equation

HRID 1801725 reaction equation
O[C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:3]=1.CN(C=O)C.C(=O)([O-])[O-].[Na+].[Na+].O=P(Cl)(Cl)[Cl:32]>>[Cl:32][C:2]1[C:7]([C:8]#[N:9])=[CH:6][N:5]=[C:4]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([O:17][CH3:18])[CH:12]=2)[N:3]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 24813Phosphorus oxychlorideHCID 178490983HCID 178490983, compound

Product 1

HCID 59823351HCID 59823351, compound

Procedure

To a solution of 4-hydroxy-2-(3-methoxyphenylamino)pyrimidine-5-carbonitrile in POCl3 was added DMF 0.5 ml. The solution was refluxed for 3 h. The reaction mixture was cooled to room temperature and poured into ice-water. The solution was adjusted to pH=8-9 by aqueous sodium carbonate solution and extracted with dichloromethane. The combined organic layers were washed with brine, dried over anhydrous Na2SO4, concentrated in vacuo to afford 4-chloro-2-(3-methoxyphenylamino)pyrimidine-5-carbonitrile.

Workup

  1. temperatureThe solution was refluxed for 3 h
  2. extractionextracted with dichloromethane
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over anhydrous Na2SO4
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-2c73666e2d264d96b7dfe40d5d07406d
Source dataset
uspto-grants-2013_01
Patent number
US08349859B2

Reaction notes

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