Dimethylamine → HCID 53851985, compound

HRID 863756Notes

Reaction equation

HRID 863756 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[C:9](=[O:10])[O:8][C:7]2(C#N)[C:12]1[N:17]=[C:16]([O:18][CH3:19])[CH:15]=[C:14]([O:20][CH3:21])[N:13]=1.[CH3:24][NH:25][CH3:26]>C1COCC1.O>[CH3:24][N:25]([CH3:26])[C:9](=[O:10])[C:11]1[C:6]([C:7]([C:12]2[N:13]=[C:14]([O:20][CH3:21])[CH:15]=[C:16]([O:18][CH3:19])[N:17]=2)=[O:8])=[CH:5][CH:4]=[CH:3][C:2]=1[Cl:1]

Participants

5

Reactant 2

HCID 674DimethylamineHCID 19050667HCID 19050667, compound

Product 1

HCID 53851985HCID 53851985, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

1.0 g of 7-chloro-3-cyano-3-(4,6-dimethoxy-2-pyrimidinyl)phthalide is dissolved in 15 ml of THF. 0.7 ml of a 40% aqueous dimethylamine solution is then added via syringe whereupon the solution darkens. Stirring is continued at R.T. for 15 minutes and the mixture diluted with water and partitioned between ethyl acetate and water. The organic phase is separated, washed with 2N H2SO4, then brine, dried and concentrated. The residue is purified on silica gel, eluant 200 ml of 50% ethyl acetate/hexane then 100% ethyl acetate. Fractions 12 to 15 yielded the title compound, m.p. 141°-142° C.

Workup

  1. custompartitioned between ethyl acetate and water
  2. customThe organic phase is separated
  3. washwashed with 2N H2SO4
  4. dry with materialbrine, dried
  5. concentrationconcentrated
  6. customThe residue is purified on silica gel, eluant 200 ml of 50% ethyl acetate/hexane

Sources & evidence

ORD record
ord-3e84bc22b3ea4b4a91d8c64b7287069a
Source dataset
uspto-grants-1996_10
Patent number
US05561101

Reaction notes

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