Butylamine → HCID 9904500, compound

HRID 728656Notes

Reaction equation

HRID 728656 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][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4](Cl)[N:3]=1.[CH2:19]([NH2:23])[CH2:20][CH2:21][CH3:22].[OH-].[Na+]>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][C@H:14]([CH2:16][OH:17])[CH:13]=[CH:12]2)=[C:4]([NH:23][CH2:19][CH2:20][CH2:21][CH3:22])[N:3]=1

Participants

5

Reactant 3

HCID 8007ButylamineHCID 14798Sodium HydroxideHCID 4514744-(2-Amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol, (1S,4R)-

Product 1

HCID 9904500HCID 9904500, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (±)-cis-4-(2-amino-6-chloro-9H-purin-9-yl)-2-cyclopentene-1-methanol from Example 4 (0.408 g, 1.5 mmol): butylamine (0.549 g, 7.5 mmol, 5 eqv.) and ethanol (10 mL) was stirred at reflux for 3 hours. The solution was allowed to cool to room temperature before the addition of 1.5 mL of 1.0 N NaOH. The solution was concentrated and the residues were purified by elution from a silica gel column with 5% methanol-chloroform (0.440 g, 97%). The title compound was dissolved in hot acetonitrile then cooled to produce a white powder, m.p. 116-118° C.

Workup

  1. temperatureat reflux for 3 hours
  2. concentrationThe solution was concentrated
  3. customthe residues were purified by elution from a silica gel column with 5% methanol-chloroform (0.440 g, 97%)
  4. dissolutionThe title compound was dissolved in hot acetonitrile
  5. temperaturethen cooled
  6. customto produce a white powder, m.p. 116-118° C.

Sources & evidence

ORD record
ord-fa44ab227d884b11babec15023a49fdb
Source dataset
uspto-grants-1991_09
Patent number
US05049671

Reaction notes

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