Formaldehyde → 4-Amino-7-(2-deoxy-beta-d-erythropentofuranosyl)-5-morpholinomethyl-7h-pyrrolo-[2,3-d]pyrimidine

HRID 1456847Notes

Reaction equation

HRID 1456847 reaction equation
[CH:1]1[C:5]2=[C:6]([NH2:10])[N:7]=[CH:8][N:9]=[C:4]2[N:3]([C@@H:11]2[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[C@H:12]2O)[CH:2]=1.[CH2:20]=O.[NH:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1>CN(C=O)C>[NH2:10][C:6]1[C:5]2[C:1]([CH2:20][N:22]3[CH2:27][CH2:26][O:25][CH2:24][CH2:23]3)=[CH:2][N:3]([C@@H:11]3[O:15][C@H:14]([CH2:16][OH:17])[C@@H:13]([OH:18])[CH2:12]3)[C:4]=2[N:9]=[CH:8][N:7]=1

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6245TubercidinHCID 8083Morpholine

Product 1

HCID 1020951944-Amino-7-(2-deoxy-beta-d-erythropentofuranosyl)-5-morpholinomethyl-7h-pyrrolo-[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

can be prepared by using the Mannich reaction. The 5-morpholinomethyl derivative (Watanabe et al., Nucleosides & Nucleotides, 1(2), 191-203, 1982) is obtained by heating tubercidin together with paraformaldehyde and morpholine in DMF. The 5-morpholine derivative (33) is obtained in accordance with the silylation and deoxygenation described in Ex. 33.

Workup

  1. customcan be prepared
  2. customthe Mannich reaction

Sources & evidence

ORD record
ord-ec76c5ebee0a489c9b11971eb5d65d8c
Source dataset
uspto-grants-1998_12
Patent number
US05844106

Reaction notes

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