Ammonia → HCID 86742689, compound

HRID 2292227Notes

Reaction equation

HRID 2292227 reaction equation
C(C1[N:11]=[CH:10][N:9]=[C:8]2[C:4]=1[NH:5][CH:6]=[N:7]2)#N.C[Si]([N:16]([Si](C)(C)C)[C:17](=O)[C:18](F)(F)F)(C)C.C(O[C@@H:31]1[O:43][C@H:42]([CH2:44][O:45]C(=O)C)[C@@H:37]([O:38]C(=O)C)[C@H:32]1[O:33]C(=O)C)(=O)C.C[Si](OS(C(F)(F)F)(=O)=O)(C)C.[NH3:61]>C(#N)C>[C@@H:31]1([NH:16][C:17]2[C:18]3[CH:4]=[N:5][CH2:6][N:7]([NH2:61])[C:8]=3[N:9]=[CH:10][N:11]=2)[O:43][C@H:42]([CH2:44][OH:45])[C@@H:37]([OH:38])[C@H:32]1[OH:33]

Participants

7

Reactant 5

HCID 222AmmoniaHCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 65367Trimethylsilyl triflateHCID 748586-CyanopurineHCID 830641,2,3,5-Tetraacetyl-beta-D-ribofuranose

Product 1

HCID 86742689HCID 86742689, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

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. temperatureunder reflux
  2. customat ambient temperature

Sources & evidence

ORD record
ord-ae06fa0b8a0b45c9a55366d585e43d88
Source dataset
uspto-grants-1989_01
Patent number
US04801698

Reaction notes

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