Benzyl isocyanate → 5-Amino-N-benzyl-7-(2Furyl)-3H-[1,2,3]Triazolo[4,5-D]Pyrimidin-3-Ylcarboxamide

HRID 732973Notes

Reaction equation

HRID 732973 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[C:7]2[NH:15][N:14]=[N:13][C:8]=2[N:9]=[C:10]([NH2:12])[N:11]=1.[CH2:16]([N:23]=[C:24]=[O:25])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>CN(C=O)C.CN(C1C=CN=CC=1)C.CCOC(C)=O>[NH2:12][C:10]1[N:11]=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[C:7]2[N:15]=[N:14][N:13]([C:24]([NH:23][CH2:16][C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)=[O:25])[C:8]=2[N:9]=1

Participants

6

Reactant 2

HCID 76639Benzyl isocyanateHCID 178508305HCID 178508305, compound

Product 1

HCID 98589295-Amino-N-benzyl-7-(2Furyl)-3H-[1,2,3]Triazolo[4,5-D]Pyrimidin-3-YlcarboxamideYield 19%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 7-(2-furyl)-1H-[1,2,3]triazolo[4,5-d]pyrimidine-5-amine (202 mg, 1.0 mmol) in DMF (3 mL) was treated with benzyl isocyanate (123 μL, 1.0 mmol) and a catalytic amount of DMAP, stirred at room temperature overnight, diluted with EtOAc and filtered to give the title compound (62 mg, 19%) as a peach coloured solid.

Workup

  1. filtrationfiltered

Sources & evidence

ORD record
ord-d1c4c325b7d04ae1b247468ac384b8b4
Source dataset
uspto-grants-2009_09
Patent number
US07589097B2

Reaction notes

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