Trimethylamine → N(6)-cyclopentyl-9-methyladenine

HRID 865357Notes

Reaction equation

HRID 865357 reaction equation
CC(OC1C=CC(C([C:18]2[CH:23]=[CH:22][C:21](OC(C)=O)=[CH:20]C=2)=C2CCCCC2)=CC=1)=O.[CH3:28][N:29]1[CH:37]=[N:36][C:35]2[C:30]1=[N:31][CH:32]=[N:33][C:34]=2[NH2:38].C1(N)CCCC1.CN(C)C>C(O)C>[CH:21]1([NH:38][C:34]2[N:33]=[CH:32][N:31]=[C:30]3[C:35]=2[N:36]=[CH:37][N:29]3[CH3:28])[CH2:20][CH2:18][CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 1146TrimethylamineHCID 2906CyclopentylamineHCID 131719616HCID 131719616, compound

Product 1

HCID 4401N(6)-cyclopentyl-9-methyladenineYield 74%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To prepare N6 -cyclopenyl-9-methyl Adenine the following additional steps were taken. A mixture of 6-chloro-9-methyl Adenine (0.82 g) , cyclopentylamine (0.52 ml) , trimethylamine (0.53 ml) and ethanol. (60 ml), was refluxed for 24 hours. The solution was concentrated in vacuo to a yellow syrup. The syrup was passed through a C-18 column to give 0.78 g or 74% yield of with m.p. 108°-109° C. 1HNMR(Me2SO-d6): δ1-2 (m, 9 H); 3.7 (S, CH3); 7.6(d,NH); 8.1(S,1H); 8.2(S,1H).

Workup

  1. temperature(60 ml), was refluxed for 24 hours
  2. concentrationThe solution was concentrated in vacuo to a yellow syrup
  3. customto give 0.78 g or 74% yield of with m.p. 108°-109° C

Sources & evidence

ORD record
ord-bb285b786787493cba191bff67f9920e
Source dataset
uspto-grants-1996_10
Patent number
US05565566

Reaction notes

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