Dimethylformamide → HCID 67849139, compound

HRID 485997Notes

Reaction equation

HRID 485997 reaction equation
[F:1][C@@H:2]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:3][CH2:4][O:5][C:6]1[CH:7]=[N:8][C:9]([C:12]2[CH:17]=[CH:16][C:15]([OH:18])=[CH:14][CH:13]=2)=[N:10][CH:11]=1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C.S(C1C=CC(C)=CC=1)(O[CH2:38][C@@H:39]([O:45][CH:46]1[CH2:51][CH2:50][CH2:49][CH2:48][O:47]1)[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])(=O)=O>O>[F:1][C@@H:2]([CH2:19][CH2:20][CH2:21][CH3:22])[CH2:3][CH2:4][O:5][C:6]1[CH:11]=[N:10][C:9]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH2:38][C@@H:39]([O:45][CH:46]3[CH2:51][CH2:50][CH2:49][CH2:48][O:47]3)[CH2:40][CH2:41][CH2:42][CH2:43][CH3:44])=[CH:14][CH:13]=2)=[N:8][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 228505822-(S)-tetrahydropyranyloxyheptyl tosylateHCID 1363783745-[3-(S)-fluoroheptyloxy]-2-(4-hydroxyphenyl)pyrimidine

Product 1

HCID 67849139HCID 67849139, compoundYield 110.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

In a reaction flask were charged 3.5 g of 5-[3-(S)-fluoroheptyloxy]-2-(4-hydroxyphenyl)pyrimidine synthesized in the same manner as in steps 1 to 7 of Example 1, 3.17 g of potassium carbonate, 70 ml of DMF, and 6.4 g of 2-(S)-tetrahydropyranyloxyheptyl tosylate in a nitrogen stream, and the mixture was allowed to react at 80° C. for one day. After cooling, water was added thereto, the reaction mixture was extracted with toluene, and the solvent was removed from the extract to obtain 7.6 g of a crude product. Purification by silica gel column chromatography gave 6.4 g of the titled compound.

Workup

  1. customto react at 80° C. for one day
  2. temperatureAfter cooling
  3. extractionthe reaction mixture was extracted with toluene
  4. customthe solvent was removed from the
  5. extractionextract
  6. customto obtain 7.6 g of a crude product
  7. customPurification by silica gel column chromatography

Sources & evidence

ORD record
ord-8566d3c36a1b400c91d2ee96d84d58da
Source dataset
uspto-grants-1994_03
Patent number
US05290477

Reaction notes

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