Phosgene → 6-(2-Furyl)-9-(1-pyrrolidinylcarbonyl)-9H-purine-2-amine

HRID 271259

Reaction equation

HRID 271259 reaction equation
[NH:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1.[C:6](Cl)(Cl)=[O:7].[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]1[NH:23][C:22]([NH2:24])=[N:21][C:20]2[C:16]=1[N:17]=[CH:18][N:19]=2.CCN(CC)CC>C1(C)C=CC=CC=1.O>[O:10]1[CH:14]=[CH:13][CH:12]=[C:11]1[C:15]1[N:23]=[C:22]([NH2:24])[N:21]=[C:20]2[C:16]=1[N:17]=[CH:18][N:19]2[C:6]([N:1]1[CH2:5][CH2:4][CH2:3][CH2:2]1)=[O:7]

Participants

7

Reactant 4

HCID 6371PhosgeneHCID 8471TriethylamineHCID 31268PyrrolidineHCID 1785082476-(furan-2-yl)-9H-purin-2-amine

Product 1

HCID 598349776-(2-Furyl)-9-(1-pyrrolidinylcarbonyl)-9H-purine-2-amineYield 62%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1140TolueneSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of pyrrolidine (50 mL, 0.6 mmol) in toluene (2 mL) was treated with a solution of phosgene in toluene (0.31 mL, 1.93-M, 0.6 mmol), heated at 80° C. for 30 mins, cooled and concentrated in vacuo. The residue was dissolved in THF (2 mL) and added to a solution of 6-(2-furyl)-1H-purine-2-amine (100 mg, 0.5 mmol) and Et3N (83 mL, 0.6 mmol) in DMP (0.5 mL), stirred at 60° C. for 16 h, poured into water and extracted with EtOAc. The combined organic phase was dried (MgSO4), concentrated in vacuo and the resulting solid triturated with EtOAc/heptane and filtered to give the title compound (92 mg, 62%) as a cream solid.

Workup

  1. temperaturecooled
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in THF (2 mL)
  4. extractionextracted with EtOAc
  5. dry with materialThe combined organic phase was dried (MgSO4)
  6. concentrationconcentrated in vacuo
  7. customthe resulting solid triturated with EtOAc/heptane
  8. filtrationfiltered

Sources & evidence

ORD record
ord-aa7f95a0fb27463884a087d55b99382d
Source dataset
uspto-grants-2008_11
Patent number
US07452894B2

Linked notes

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