4,6-Dichloropyrimidine → HCID 53776090, compound

HRID 1080442Notes

Reaction equation

HRID 1080442 reaction equation
[CH3:1][O:2][C:3]1[CH:17]=[CH:16][C:6]2[C:7]([N:10]3[CH2:15][CH2:14][NH:13][CH2:12][CH2:11]3)=[N:8][O:9][C:5]=2[CH:4]=1.[Cl:18][C:19]1[CH:24]=[C:23](Cl)[N:22]=[CH:21][N:20]=1.C(=O)(O)[O-].[Na+]>C(O)C>[Cl:18][C:19]1[N:20]=[C:21]([N:13]2[CH2:12][CH2:11][N:10]([C:7]3[C:6]4[CH:16]=[CH:17][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[O:9][N:8]=3)[CH2:15][CH2:14]2)[N:22]=[CH:23][CH:24]=1

Participants

5

Reactant 3

HCID 709434,6-DichloropyrimidineHCID 516892Sodium BicarbonateHCID 10988161HCID 10988161, compound

Product 1

HCID 53776090HCID 53776090, compoundYield 97.1%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A stirred solution of 6-methoxy-3-(1-piperazinyl)-1,2-benzisoxazole (1.0 g), 4,6-dichloropyrimidine (0.64 g) and sodium bicarbonate (1.08 g) were refluxed in absolute ethanol under N2 for 90 minutes. TLC (silica gel 2/1 acetone/heptane) showed no presence of starting material. The reaction was allowed to cool to room temperature, partitioned between CH2Cl2 and water, extracted with CH2Cl2, dried over MgSO4 and concentrated in vacuo to afford 1.44 g of material. The material was further purified through recrystallization from CH2Cl2 /pet. ether to yield the product 1.1 g, m.p. 203°-204° C.

Workup

  1. custompartitioned between CH2Cl2 and water
  2. extractionextracted with CH2Cl2
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-d7ea5e07cf7b4fcbb5fb8e342625b26c
Source dataset
uspto-grants-1996_12
Patent number
US05580982

Reaction notes

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