Triethylamine → 6-[(R)-2-(naphthalen-1-yloxymethyl)pyrrolidin-1-yl]-9H-purine

HRID 81388Notes

Reaction equation

HRID 81388 reaction equation
Cl[C:2]1[N:10]=[CH:9][N:8]=[C:7]2[C:3]=1[NH:4][CH:5]=[N:6]2.[C:11]1([O:21][CH2:22][CH:23]2[CH2:27][CH2:26][CH2:25][NH:24]2)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1.C(N(CC)CC)C>C(O)CCC>[C:11]1([O:21][CH2:22][C@H:23]2[CH2:27][CH2:26][CH2:25][N:24]2[C:2]2[N:10]=[CH:9][N:8]=[C:7]3[C:3]=2[N:4]=[CH:5][NH:6]3)[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[CH:14]=[CH:13][CH:12]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 53592776-ChloropurineHCID 616860752(-Naphthalen-1-yloxymethyl)pyrrolidine

Product 1

HCID 1784199826-[(R)-2-(naphthalen-1-yloxymethyl)pyrrolidin-1-yl]-9H-purine

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

1.6 235 mg of 6-chloropurine, 400 mg of 2(-naphthalen-1-yloxymethyl)pyrrolidine and 0.8 ml of triethylamine are dissolved in 30 ml of 1-butanol and irradiated in the microwave at 120° C. for 6 h. After removal of the solvent in vacuo, the residue is taken up in 10 ml of methanol, the crystals which precipitate in the process are filtered off with suction and washed with methanol, giving 340 mg of colourless crystals 6-[(R)-2-(naphthalen-1-yloxymethyl)pyrrolidin-1-yl]-9H-purine (“A1”); Rt.: 1.806 min; [M+H]+346; m.p. 207-208°;

Workup

  1. customirradiated in the microwave at 120° C. for 6 h
  2. customAfter removal of the solvent in vacuo
  3. customthe crystals which precipitate in the process
  4. filtrationare filtered off with suction
  5. washwashed with methanol

Sources & evidence

ORD record
ord-abf86579acdf4870b2a92663ead5ad46
Source dataset
uspto-grants-2014_09
Patent number
US08846694B2

Reaction notes

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