Dicyclohexylcarbodiimide → HCID 21270712, compound

HRID 1193919Notes

Reaction equation

HRID 1193919 reaction equation
C1(N=C=NC2CCCCC2)CCCCC1.[Cl:16][C:17]1[C:22]([OH:23])=[CH:21][C:20]([N:24]2[C:29](=[O:30])[C:28]([F:31])=[C:27]([C:32]([F:38])([F:37])[C:33]([F:36])([F:35])[F:34])[N:26]=[C:25]2[O:39][CH3:40])=[C:19]([F:41])[CH:18]=1.[C:42](O)(=[O:47])[CH2:43][CH2:44][C:45]#[CH:46].N1(C2C=CN=CC=2)CCCC1>C(Cl)Cl>[C:42]([O:23][C:22]1[CH:21]=[C:20]([N:24]2[C:29](=[O:30])[C:28]([F:31])=[C:27]([C:32]([F:37])([F:38])[C:33]([F:34])([F:36])[F:35])[N:26]=[C:25]2[O:39][CH3:40])[C:19]([F:41])=[CH:18][C:17]=1[Cl:16])(=[O:47])[CH2:43][CH2:44][C:45]#[CH:46]

Participants

6

Reactant 4

HCID 10868DicyclohexylcarbodiimideHCID 224644-Pentynoic acidHCID 755674-PyrrolidinopyridineHCID 21270789HCID 21270789, compound

Product 1

HCID 21270712HCID 21270712, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.74 g of N,N'-dicyclohexylcarbodiimide is added while stirring at room temperature to a solution of 1.60 g of 1-(4-chloro-2-fluoro-5-hydroxyphenyl)-5-fluoro-2-methoxy-4-pentafluoroethyl-6(1H)-pyrimidinone, 0.30 g of 4-pentynoic acid and 0.05 g of 4-pyrrolidino-pyridine in 50 ml of methylene chloride and the mixture is stirred at room temperature for 5 hours. Insoluble constituents are subsequently filtered off under suction and the filtrate is evaporated to dryness. The residue is purified by chromatography on a silica gel column using n-hexane/diethyl ether (3:1) as the eluent. The product is recrystallized from n-hexane/diethyl ether. There is obtained 2-chloro-4-fluoro-5-[5-fluoro-2 -methoxy-6-oxo-4-pentafluoroethyl-1(6H)-pyrimidinyl]-phenyl 4-pentynoate, m.p. 107°-109° C.

Workup

  1. filtrationInsoluble constituents are subsequently filtered off under suction
  2. customthe filtrate is evaporated to dryness
  3. customThe residue is purified by chromatography on a silica gel column
  4. customThe product is recrystallized from n-hexane/diethyl ether

Sources & evidence

ORD record
ord-3ad9a1c42e354c6e9b5fa60b75cd30be
Source dataset
uspto-grants-1989_03
Patent number
US04812164

Reaction notes

Loading…