Butyl isocyanate → 2-Amino-N-n-butyl-6-(2-furyl)-9H-purine-9-carboxamide

HRID 271257

Reaction equation

HRID 271257 reaction equation
[O:1]1[CH:5]=[CH:4][CH:3]=[C:2]1[C:6]1[NH:14][C:13]([NH2:15])=[N:12][C:11]2[C:7]=1[N:8]=[CH:9][N:10]=2.[CH2:16]([N:20]=[C:21]=[O:22])[CH2:17][CH2:18][CH3:19]>CN(C1C=CN=CC=1)C.CN(C=O)C>[NH2:15][C:13]1[N:12]=[C:11]2[C:7]([N:8]=[CH:9][N:10]2[C:21]([NH:20][CH2:16][CH2:17][CH2:18][CH3:19])=[O:22])=[C:6]([C:2]2[O:1][CH:5]=[CH:4][CH:3]=2)[N:14]=1

Participants

5

Reactant 2

HCID 8110Butyl isocyanateHCID 1785082476-(furan-2-yl)-9H-purin-2-amine

Product 1

HCID 99441512-Amino-N-n-butyl-6-(2-furyl)-9H-purine-9-carboxamideYield 100%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
65 °C

Procedure

A solution of 6-(2-furyl)-1H-purine-2-amine (0.050 g, 0.25 mmol) and DMAP (5 mg, 0.03 mmol) in anhydrous DMF (1 μL) was treated with n-butylisocyanate (0.029 g, 0.30 mmol), shaken at 65° C. for 1 h, poured onto ice-cold water (10 mL), cooled at 0° C. for 15 min and the resulting precipitate filtered and dried in vacuo over P2O5 to give the title compound (74 mg, 100%) as a white solid.

Workup

  1. additionpoured onto ice-cold water (10 mL)
  2. temperaturecooled at 0° C. for 15 min
  3. filtrationthe resulting precipitate filtered
  4. dry with materialdried in vacuo over P2O5

Sources & evidence

ORD record
ord-692e9921ab9a4a878d1a098fd1e3fa5d
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Linked notes

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