2-Aminopyridine → 6-Amino-4-(2-furyl)-N-(2-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-1-ylacetamide

HRID 8297

Reaction equation

HRID 8297 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]([OH:14])=O)[N:9]=[CH:10][C:5]2=[C:4]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[N:3]=1.[C:20]([C:27]1[NH:28][CH:29]=[CH:30][N:31]=1)([C:22]1NC=CN=1)=O.NC1C=CC=CN=1>CN(C=O)C.O>[NH2:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:11][C:12]([NH:28][C:27]3[CH:20]=[CH:22][CH:29]=[CH:30][N:31]=3)=[O:14])[N:9]=[CH:10][C:5]2=[C:4]([C:15]2[O:16][CH:17]=[CH:18][CH:19]=2)[N:3]=1

Participants

6

Reactant 3

HCID 104392-AminopyridineHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 220155316-Amino-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidin-1-ylacetic acid

Product 1

HCID 235468936-Amino-4-(2-furyl)-N-(2-pyridyl)-1H-pyrazolo[3,4-d]pyrimidin-1-ylacetamideYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 6-amino-4-(2-furyl)-1H-pyrazolo[3,4-d]pyrimidin-1-ylacetic acid (200 mg, 0.77 mmol) in DMF (3 mL) was treated with carbonyl diimidazole (125 mg, 0.77 mmol), stirred at room temperature for 2 h, treated with 2-aminopyridine (72 mg, 0.77 mmol), heated to 50° C. for 3 h, cooled and diluted with water. The resulting white solid was filtered, suspended in MeOH, treated with HCl in dioxan (4-M, 1 mL) diluted with diethyl ether and filtered to give the title compound (187 mg, 59%) as a yellow solid.

Workup

  1. temperatureheated to 50° C. for 3 h
  2. temperaturecooled
  3. filtrationThe resulting white solid was filtered
  4. additiontreated with HCl in dioxan (4-M, 1 mL)
  5. additiondiluted with diethyl ether
  6. filtrationfiltered

Sources & evidence

ORD record
ord-b725349e98b84660a46287b12d70b9d9
Source dataset
uspto-grants-2006_08
Patent number
US07087754B2

Linked notes

Loading…