Dimethylformamide → HCID 67762623, compound

HRID 342479Notes

Reaction equation

HRID 342479 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].[Cl:14][C:15]1[C:16]([NH:23][CH:24]2[CH2:39][CH2:38][C:27]3([O:31][CH:30]([CH2:32][O:33]S(C)(=O)=O)OC3)[CH2:26][CH2:25]2)=[N:17][CH:18]=[N:19][C:20]=1[CH2:21][CH3:22].[CH3:40]N(C)C=O>O.ClCCl>[Cl:14][C:15]1[C:16]([NH:23][CH:24]2[CH2:25][CH2:26][C:27]3([O:31][CH:30]([CH2:9][O:8][C:5]4[CH:6]=[CH:7][C:2]([O:1][CH3:40])=[CH:3][CH:4]=4)[CH2:32][O:33]3)[CH2:38][CH2:39]2)=[N:17][CH:18]=[N:19][C:20]=1[CH2:21][CH3:22]

Participants

7

Reactant 5

HCID 6228Dimethylformamide2×HCID 90154-MethoxyphenolHCID 24758Sodium hydrideHCID 86753548HCID 86753548, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 67762623HCID 67762623, compound

Reagents, catalysts & solvents 1

HCID 21908982Water methylene chlorideSolvent

Procedure

1.17 g (94 mmol) of 4-hydroxyanisole were added, a little at a time, to a suspension of 0.28 g (9.4 mmol) of 80% sodium hydride (dispersion in oil) in 25 ml of dimethylformamide, and the mixture was stirred until the evolution of hydrogen had ceased, a solution of 1.90 g (47 mmol) of 5-chloro-6-ethyl-4-(2-methylsulfonyloxymethyl-1,3-dioxaspiro[4.5]dec-8-ylamino!pyrimidine (Example G) in a small amount of dimethylformamide was subsequently added dropwise, and stirring of the mixture was continued at 100° C. for 6 hours. After the solvent had been stripped off, the mixture was taken up in water/dichloromethane and extracted by stirring with dilute sodium hydroxide solution and with water, and the organic phase was dried and concentrated. The crude product was chromatographed on silica gel (eluent ethyl acetate/methanol 9:1). This gave 1.3 g (68.6% of theory) of a colorless oil (isomer mixture).

Workup

  1. extractionextracted
  2. stirringby stirring with dilute sodium hydroxide solution and with water
  3. customthe organic phase was dried
  4. concentrationconcentrated
  5. customThe crude product was chromatographed on silica gel (eluent ethyl acetate/methanol 9:1)

Sources & evidence

ORD record
ord-3016f771ee3d465d92a0dbc41d527f85
Source dataset
uspto-grants-1999_01
Patent number
US05859009

Reaction notes

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