2-Chloro-4-[2-(4-fluorophenyl)ethynyl]pyrimidine → HCID 86761634, compound

HRID 2063255Notes

Reaction equation

HRID 2063255 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8]#[C:9][C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[CH:5]=[CH:4][N:3]=1.OC1O[N:20]=[N+:21]2[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)=[O:28])[CH2:23][C:22]=12>C1(C)C=C(C)C=C(C)C=1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]2[C:9]([C:10]3[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=3)=[N:20][N:21]3[CH2:26][CH2:25][N:24]([C:27]([O:29][CH2:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[O:28])[CH2:23][C:22]=23)[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 2

HCID 121652312-Chloro-4-[2-(4-fluorophenyl)ethynyl]pyrimidineHCID 178525150HCID 178525150, compound2×

Product 1

HCID 86761634HCID 86761634, compound

Reagents, catalysts & solvents 1

HCID 7947MesityleneSolvent

Conditions

Temperature
165 °C

Procedure

A mixture of 2-chloro-4-[2-(4-fluorophenyl)ethynyl]pyrimidine (i.e. the product of Example 2, Step A) (2.51 g, 10.8 mmol) and 4,5,6,7-tetrahydro-3-hydroxy-5-[(phenylmethoxy)carbonyl][1,2,3]oxadiazolo[3,4-a]pyrazin-8-ium inner salt (i.e. the product of Step B) (3.00 g, 10.8 mmol) in mesitylene (100 mL) was stirred at 165° C. for 18 h. The reaction mixture was cooled and concentrated under reduced pressure. The residue was diluted with dichloromethane (50 mL) and treated with silica gel (10.0 g). The silica gel suspension was concentrated under reduced pressure to leave a mixture of silica gel and crude product, which was purified by silica gel chromatography using a gradient of ethyl acetate/hexanes (0:1 to 1:1) as eluant to give 1.5 g of the title compound as a white solid.

Workup

  1. temperatureThe reaction mixture was cooled
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue was diluted with dichloromethane (50 mL)
  4. additiontreated with silica gel (10.0 g)
  5. concentrationThe silica gel suspension was concentrated under reduced pressure
  6. customto leave
  7. additiona mixture of silica gel and crude product, which
  8. customwas purified by silica gel chromatography

Sources & evidence

ORD record
ord-8703ff0cadfb4f95b508d568eff84bfe
Source dataset
uspto-grants-2012_10
Patent number
US08288375B2

Reaction notes

Loading…