Cyclopropylamine → 280138-71-8

HRID 2118090Notes

Reaction equation

HRID 2118090 reaction equation
[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][O:14][C@@H:13]([CH2:16][OH:17])[O:12]2)=[C:4](Cl)[N:3]=1.[CH:19]1([NH2:22])[CH2:21][CH2:20]1>C(O)C>[NH2:1][C:2]1[N:10]=[C:9]2[C:5]([N:6]=[CH:7][N:8]2[C@H:11]2[CH2:15][O:14][C@@H:13]([CH2:16][OH:17])[O:12]2)=[C:4]([NH:22][CH:19]2[CH2:21][CH2:20]2)[N:3]=1

Participants

4

Reactant 2

HCID 69828CyclopropylamineHCID 454987HCID 454987, compound

Product 1

HCID 485995280138-71-8Yield 77%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
0 °C

Procedure

[4(R)-(2-Amino-6-chloro-purin-9-yl)-[1,3]dioxolan-2(R)-yl]-methanol (1.2 kg, 4.5 moles), ethanol (15.2 L) and cyclopropylamine (756 g) were refluxed under nitrogen for 16 hours. The reaction was monitored for completion by HPLC. Once completed the reaction mixture was hot-filtered and allowed to cool to 0° C. slowly. The solids were filtered and subsequently recrystallized from ethanol to give [4(R)-(2-Amino-6-cyclopropylamino-purin-9-yl)-[1,3]dioxolan-2(R)-yl]-methanol (1.0 kg, 77%).

Workup

  1. filtrationwas hot-filtered
  2. filtrationThe solids were filtered
  3. customsubsequently recrystallized from ethanol

Sources & evidence

ORD record
ord-7804342d7d56448e814b975f7d1e1f09
Source dataset
uspto-grants-2008_10
Patent number
US07442813B2

Reaction notes

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