Lithium Chloride → 5-(1-(t-Butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

HRID 897405Notes

Reaction equation

HRID 897405 reaction equation
Cl[C:2]1[N:7]2[CH:8]=[N:9][N:10]=[C:6]2[C:5]([C:11]2[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=2)=[C:4]([C:21]2[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=2)[N:3]=1.[C:28]([O:32][C:33]([N:35]1[CH2:40][CH:39]=[C:38](OS(C(F)(F)F)(=O)=O)[CH2:37][CH2:36]1)=[O:34])([CH3:31])([CH3:30])[CH3:29].[Cl-].[Li+].C[Sn](C)C.C[Sn](C)C.[F-].[K+]>O1CCOCC1.C1(P([Pd](P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)P(C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[C:28]([O:32][C:33]([N:35]1[CH2:36][CH:37]=[C:38]([C:2]2[N:7]3[CH:8]=[N:9][N:10]=[C:6]3[C:5]([C:11]3[CH:16]=[CH:15][CH:14]=[C:13]([C:17]([F:20])([F:19])[F:18])[CH:12]=3)=[C:4]([C:21]3[CH:26]=[CH:25][N:24]=[C:23]([Cl:27])[CH:22]=3)[N:3]=2)[CH2:39][CH2:40]1)=[O:34])([CH3:31])([CH3:29])[CH3:30]

Participants

8

Reactant 5

HCID 433294Lithium ChlorideHCID 522689Potassium FluorideHCID 6327618HexamethylditinHCID 10991161Tert-butyl 4-(trifluoromethanesulfonyloxy)-1,2,3,6-tetrahydropyridine-1-carboxylateHCID 223466035-Chloro-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

Product 1

HCID 223465805-(1-(t-Butoxycarbonyl)-1,2,3,6-tetrahydropyrid-4-yl)-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine

Reagents, catalysts & solvents 2

HCID 178420554HCID 178420554, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

5-Chloro-7-(2-chloro-4-pyridyl)-8-(3-(trifluoromethyl)phenyl)-1,2,4-triazolo[4,3-c]pyrimidine (2.0 g, 5.0 mmol), 1-(t-butoxycarbonyl)-4-(trifluoromethyl sulfonyloxy)-1,2,3,6-tetrahydropyridine (2.0 g, 6.0 mmol), lithium chloride (6.64 g, 15.0 mmol), hexamethylditin (2.0 g, 6.0 mmol) and tetrakistriphenylphosphinopalladium (0.3 g, 0.25 mmol) were combined in dioxane (25 ml) and the resulting solution was heated to 90° C. for 18 hours. The mixture was added to aq. KF and was stirred for 2 hours and then partitioned with methylene chloride. The organic layer was dried over sodium sulfate, filtered and concentrated to a syrup. Purification by column chromatography on silica gel (30% ethyl acetate in hexane) gave the product as a syrup; MS m/z (M+H)+ 557.2; C27H24F3ClN6O2 require 556.2.

Workup

  1. custompartitioned with methylene chloride
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to a syrup
  5. customPurification by column chromatography on silica gel (30% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-dc929cbb45904f4a900e43af13b3a269
Source dataset
uspto-grants-2005_07
Patent number
US06921762B2

Reaction notes

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