Phosphorus oxychloride → HCID 86742690, compound

HRID 2292228Notes

Reaction equation

HRID 2292228 reaction equation
[C@@H]1([NH:10][C:11]2[C:20]3[CH:19]=[N:18][CH2:17][N:16]([NH2:21])[C:15]=3[N:14]=[CH:13][N:12]=2)O[C@H](CO)[C@@H](O)[C@H]1O.P(Cl)(Cl)(Cl)=O>COP(OC)(OC)=O>[N:14]1[C:15]2[N:16]([NH2:21])[CH2:17][N:18]=[CH:19][C:20]=2[C:11]([NH2:10])=[N:12][CH:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 86742689HCID 86742689, compound

Product 1

HCID 86742690HCID 86742690, compound

Reagents, catalysts & solvents 1

HCID 10541Trimethyl PhosphateSolvent

Procedure

The method of this invention comprises the steps of a) reacting 6-cyanopurine with bis(trimethylsilyl)trifluoroacetamide in acetonitrile under reflux and thereafter with tetra-O-acetyl-β-D-ribofuranose in the presence of trimethylsilyltrifluoromethanesulfonate to stereospecifically produce 9-(tri-O-acetyl-β-D-ribofuranosyl)-6-cyanopurine in high yield; b) reacting said 9-(tri-O-acetyl-β-D-ribofuranosyl)-6-cyanopurine with methanolic ammonia in a sealed pressure vessel at ambient temperature to produce N4 -(β-D-ribofuranosyl)pyrimido[4,5-d]pyrimidine-4,8-diamine; c) reacting said N4 -(β-D-ribofuranosyl)pyrimido[4,5-d]pyrimidine-4,8-diamine with phosphoryl chloride in trimethylphosphate at a temperature below about 10° C. to produce N4 -5-O-phosphono-β-D-ribofuranosyl)pyrimido[4,5-d]pyrimidine-4,8-diamine or, alternatively reacting said N4 -(β-D-ribofuranosyl)pyrimido[4,5-d]pyrimidine-4,8-diamine with acetic anhydride in the presence of an acid scavenger to produce N4 -(2,3,5-tri-O-acetyl-β-D-ribofuranoxyl)pyrimido[4,5-d]pyrimidine-4,8-diamine.

Workup

  1. customat a temperature below about 10° C.

Sources & evidence

ORD record
ord-fe477d3e1df0470da804916265467b1f
Source dataset
uspto-grants-1989_01
Patent number
US04801698

Reaction notes

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