Heptanoic Acid → 2,3-Difluoro-4-[5-(6-octyloxypyridin-3-yl)pyrimidin-2-yl]phenyl heptanoate

HRID 376774Notes

Reaction equation

HRID 376774 reaction equation
C1CCC(N=C=NC2CCCCC2)CC1.[F:16][C:17]1[C:22]([F:23])=[C:21]([OH:24])[CH:20]=[CH:19][C:18]=1[C:25]1[N:30]=[CH:29][C:28]([C:31]2[CH:32]=[N:33][C:34]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:35][CH:36]=2)=[CH:27][N:26]=1.[C:46](O)(=[O:53])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]>CN(C1C=CN=CC=1)C.ClCCl>[C:46]([O:24][C:21]1[CH:20]=[CH:19][C:18]([C:25]2[N:30]=[CH:29][C:28]([C:31]3[CH:32]=[N:33][C:34]([O:37][CH2:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH3:45])=[CH:35][CH:36]=3)=[CH:27][N:26]=2)=[C:17]([F:16])[C:22]=1[F:23])(=[O:53])[CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH3:52]

Participants

6

Reactant 3

HCID 8094Heptanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 1355974452-(2,3-Difluoro-4-hydroxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine

Product 1

HCID 536635672,3-Difluoro-4-[5-(6-octyloxypyridin-3-yl)pyrimidin-2-yl]phenyl heptanoateYield 84%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

2.7 mmol of DCC are introduced at room temperature into 50 ml of dichloromethane, and 2.4 mmol of 2-(2,3-difluoro-4-hydroxyphenyl)-5-(6-octyloxypyridin-3-yl)pyrimidine, 2.7 mmol of heptanoic acid and 0.24 mmol of DMAP are added. The reaction mixture is left to stand overnight with exclusion of light, precipitated dicyclohexylurea is then filtered off, and the solvent is removed in vacuo. The crude product is chromatographed on silica gel 60 using dichloromethane/ethyl acetate 20:1 (v/v) as eluent and is recrystallized from acetonitrile, giving 1.0 g (84%) of colorless crystals, X 88 SC 165 SA 167.5 I.

Workup

  1. additionare added
  2. waitThe reaction mixture is left
  3. customprecipitated dicyclohexylurea
  4. filtrationis then filtered off
  5. customthe solvent is removed in vacuo
  6. customThe crude product is chromatographed on silica gel 60 using dichloromethane/ethyl acetate 20:1 (v/v) as eluent
  7. customis recrystallized from acetonitrile

Sources & evidence

ORD record
ord-639f839adc1d4fd6bd4c86c5a1614cff
Source dataset
uspto-grants-2000_02
Patent number
US06022492

Reaction notes

Loading…