2-Chloroadenosine → 2-((2-Cyclohexylethyl)amino)adenosine

HRID 1087010Notes

Reaction equation

HRID 1087010 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH2:20])[C:5]2[N:6]=[CH:7][N:8]([C:18]=2[N:19]=1)[C@@H:9]1[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]1[OH:11].[CH:21]1([CH2:27][CH2:28][NH2:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1>C(O)C.C1OC1C>[CH:21]1([CH2:27][CH2:28][NH:29][C:2]2[N:3]=[C:4]([NH2:20])[C:5]3[N:6]=[CH:7][N:8]([C:18]=3[N:19]=2)[C@@H:9]2[O:17][C@H:14]([CH2:15][OH:16])[C@@H:12]([OH:13])[C@H:10]2[OH:11])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1

Participants

5

Reactant 2

HCID 89742-ChloroadenosineHCID 205092-Cyclohexylethylamine

Product 1

HCID 1301992-((2-Cyclohexylethyl)amino)adenosine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 6378Propylene OxideSolvent

Procedure

A mixture of 2-chloroadenosine (15.05 g) and 2-cyclohexylethylamine (31.75 g) is stirred under nitrogen at 140° over 6 hours. The reaction mixture is cooled to room temperature, diluted with ethanol (500 ml), propylene oxide (50 ml) is added and the mixture is stirred at room temperature for 3 hours. The solid is collected by vacuum filtration, washed with ethanol, then ether, and dried at 80°/0.1 mm over 16 hours. The white solid obtained is recrystallized from ethanol to yield 2-(2-cyclohexylethylamino)-adenosine, the compound of example 4q, m.p. 142°-145°, [alpha]D25 -30.5° (c=1, dimethyl sulfoxide).

Workup

  1. additionis added
  2. stirringthe mixture is stirred at room temperature for 3 hours
  3. filtrationThe solid is collected by vacuum filtration
  4. washwashed with ethanol
  5. dry with materialether, and dried at 80°/0.1 mm over 16 hours
  6. customThe white solid obtained
  7. customis recrystallized from ethanol

Sources & evidence

ORD record
ord-ee116d79171643df993f3d91b3b0fcc7
Source dataset
uspto-grants-1991_07
Patent number
US05034381

Reaction notes

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