2-Chloropyridin-4-amine → HCID 58268946, compound

HRID 1428189Notes

Reaction equation

HRID 1428189 reaction equation
CC([O-])=O.[K+].CC1(C)C(C)(C)OB([C:14]2[CH:15]=[N:16][N:17]3[CH:22]=[CH:21][CH:20]=[N:19][C:18]=23)O1.Cl[C:25]1[CH:30]=[C:29]([NH2:31])[CH:28]=[CH:27][N:26]=1>O1CCOCC1>[N:16]1[N:17]2[CH:22]=[CH:21][CH:20]=[N:19][C:18]2=[C:14]([C:25]2[CH:30]=[C:29]([NH2:31])[CH:28]=[CH:27][N:26]=2)[CH:15]=1

Participants

5

Reactant 3

HCID 844322-Chloropyridin-4-amineHCID 517044Potassium AcetateHCID 58268917Pyrazolo[1,5-a]pyrimidine-3-boronic acid pinacol ester

Product 1

HCID 58268946HCID 58268946, compoundYield 31%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
120 °C

Procedure

A suspension of 10 ml 1,4-dioxane and 8 ml 4N KOAc (5.9 g) with 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazolo[1,5-a]pyrimidine (13 g, 3.68 g) and 2-chloro-4-aminopyridine (3.68 g) was purged with nitrogen for 30 min. Then, to the suspension was added Pd(PPh3)4 (867 mg) and the reaction mixture was heated at 120° C. in microwave for 20 min. Upon cooling, the precipitated solid was filtered and used without further purification (1.0 g, 31% yield).

Workup

  1. customwas purged with nitrogen for 30 min
  2. additionThen, to the suspension was added Pd(PPh3)4 (867 mg)
  3. temperatureUpon cooling
  4. filtrationthe precipitated solid was filtered
  5. customused without further purification (1.0 g, 31% yield)

Sources & evidence

ORD record
ord-38cf5018afd04bf584960fcebbdcfd14
Source dataset
uspto-grants-2015_01
Patent number
US08937064B2

Reaction notes

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