Trimethyl Phosphate → HCID 86742692, compound

HRID 2292230Notes

Reaction equation

[C@@H:1]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:7][C@H:6]([CH2:8][OH:9])[C@@H:4]([OH:5])[C@H:2]1[OH:3].P(Cl)(Cl)(Cl)=O.C[O:28][P:29](OC)([O:31]C)=[O:30]>>[P:29]([O:9][CH2:8][C@H:6]1[O:7][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)[C@H:2]([OH:3])[C@@H:4]1[OH:5])([OH:31])([OH:30])=[O:28]

Participants

Reactant 3

HCID 10541Trimethyl Phosphate

HCID 24813Phosphorus oxychloride

HCID 86742689HCID 86742689, compound

Product 1

HCID 86742692HCID 86742692, compound

Procedure

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-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 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.

Workup

customat a temperature below about 10° C.

Sources & evidence

ORD record: ord-a0fd9a25986c4c1bb883bce527ed9e88
Source dataset: uspto-grants-1989_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04801698

Reaction notes

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