Pentanoic Acid → HCID 15027169, compound

HRID 326511Notes

Reaction equation

HRID 326511 reaction equation
[CH2:1]([C:12]1[N:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([OH:24])=[C:20]([F:25])[CH:19]=2)=[CH:14][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11].[C:26](O)(=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30].C1(N=C=NC2CCCCC2)CCCCC1.N1(C2C=CN=CC=2)CCCC1>ClCCl>[CH2:1]([C:12]1[N:17]=[CH:16][C:15]([C:18]2[CH:23]=[CH:22][C:21]([O:24][C:26](=[O:31])[CH2:27][CH2:28][CH2:29][CH3:30])=[C:20]([F:25])[CH:19]=2)=[CH:14][N:13]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH3:11]

Participants

6

Reactant 4

HCID 7991Pentanoic AcidHCID 10868DicyclohexylcarbodiimideHCID 755674-PyrrolidinopyridineHCID 19734917HCID 19734917, compound

Product 1

HCID 15027169HCID 15027169, compoundYield 76.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In a 200 ml-round bottom flask, 2.00 g (5.81 mM) of 2-undecyl-5-(3-fluoro-4-hydroxyphenyl)pyrimidine, 0.60 g (5.87 mM) of valeric acid and 50 ml of dichloromethane were placed and dissolved. To the solution, 1.21 g (5.86 mM) of N,N'-dicyclohexylcarbodiimide and 0.10 g of 4-pyrrolidinopyridine were successively added under stirring at room temperature, followed by further stirring for 4 hours and 45 minutes at room temperature. After stirring, the mixture was left standing at room temperature to precipitate N,N'-dicyclohexylurea. The resultant, N,N'-dichclohexylurea was filtered off and the solvent of the filtrate was distilled-off under reduced pressure. The residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1) and recrystallized two times from a minute solvent of acetone-methanol to obtain 1.91 g of 2-undecyl-5-(3-fluoro-4-pentanoyloxyphenyl)pyrimidine (Yield: 76.8). ##STR28##

Workup

  1. dissolutiondissolved
  2. stirringby further stirring for 4 hours and 45 minutes at room temperature
  3. stirringAfter stirring
  4. waitthe mixture was left
  5. customstanding at room temperature
  6. customto precipitate N,N'-dicyclohexylurea
  7. filtrationThe resultant, N,N'-dichclohexylurea was filtered off
  8. customThe residue was purified by silica gel column chromatography (eluent: toluene/ethyl acetate=100/1)
  9. customrecrystallized two times from a minute solvent of acetone-methanol

Sources & evidence

ORD record
ord-e8f9c3913b0a4585bdb36b2da2029345
Source dataset
uspto-grants-1993_12
Patent number
US05269964

Reaction notes

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