Acetic Acid → HCID 60204510, compound

HRID 2267389Notes

Reaction equation

HRID 2267389 reaction equation
[Li]CCCC.[F:6][C:7]1[CH:12]=[CH:11][C:10]([N:13]([CH3:19])[C:14]2[S:18][CH:17]=[N:16][CH:15]=2)=[CH:9][CH:8]=1.[Cl:20][C:21]1[N:26]=[CH:25][C:24]([F:27])=[CH:23][N:22]=1.CC(O)=O.ClC1C(=O)C(C#N)=C(C#N)C(=O)C=1Cl>CCCCCC.C1COCC1.O>[Cl:20][C:21]1[N:26]=[C:25]([C:17]2[S:18][C:14]([N:13]([C:10]3[CH:9]=[CH:8][C:7]([F:6])=[CH:12][CH:11]=3)[CH3:19])=[CH:15][N:16]=2)[C:24]([F:27])=[CH:23][N:22]=1

Participants

9

Reactant 5

HCID 176Acetic AcidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 5834662-Chloro-5-fluoropyrimidineHCID 60204509HCID 60204509, compoundHCID 178418339Butyllithium

Product 1

HCID 60204510HCID 60204510, compound

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Conditions

Temperature
-78 °C

Procedure

2.1 mL (5.3 mmol) of a 2.5 M solution of nBuLi in hexane was added to a stirred solution of 1.0 g (4.8 mmol) of N-(4-fluorophenyl)-N-methylthiazol-5-amine in 30 mL of THF at −78° C. The solution was stirred for 30 min at −78° C. before 0.61 mL (5.3 mmol) of 2-chloro-5-fluoropyrimidine was added. The reaction solution was stirred for 1 h at −78° C., then quenched by addition of 0.83 mL (14 mmol) of AcOH. A solution of 2,3-dichloro-5,6-dicyano-1,4-benzoquinone (1.1 g, 4.8 mmol) in 5 mL of THF was added and the reaction solution was warmed to 0° C. and stirred for 10 min then poured into 600 mL of water and the solid product was collected by filtration, washed with water and dried in vacuo. MS (M+H)+ 339.

Workup

  1. additionwas added
  2. temperaturethe reaction solution was warmed to 0° C.
  3. stirringstirred for 10 min
  4. filtrationthe solid product was collected by filtration
  5. washwashed with water
  6. customdried in vacuo

Sources & evidence

ORD record
ord-c06334d16a0743079d3021d60bae0300
Source dataset
uspto-grants-2010_12
Patent number
US07858785B2

Reaction notes

Loading…