Phosphorus oxychloride → HCID 105447305, compound

HRID 1427366Notes

Reaction equation

HRID 1427366 reaction equation
[OH:1][C:2]1[C:3]2[CH2:12][N:11](C(OCC3C=CC=CC=3)=O)[CH2:10][CH2:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1.Cl[C:24]1[C:25]2CN(C(OCC3C=CC=CC=3)=O)CCC=2N=C(C)N=1.P(Cl)(Cl)(Cl)=O>>[CH2:24]([O:1][C:2]1[C:3]2[CH2:12][NH:11][CH2:10][CH2:9][C:4]=2[N:5]=[C:6]([CH3:8])[N:7]=1)[CH3:25]

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 117678406HCID 117678406, compoundHCID 178433417HCID 178433417, compound

Product 1

HCID 105447305HCID 105447305, compound

Procedure

Benzyl 4-hydroxy-2-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate, which may be prepared using the general method of E. Kretzschmar and P. Meisel, Pharmazie 1988, 43, 475-476, was converted to benzyl 4-chloro-2-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate via treatment with phosphorus oxychloride. Chloride displacement with sodium ethoxide was followed by hydrogenolytic removal of the protecting group to afford the requisite 4-ethoxy-2-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine.

Workup

  1. customChloride displacement with sodium ethoxide was followed by hydrogenolytic removal of the protecting group

Sources & evidence

ORD record
ord-7f5247888a824dec9b78fc08c3e36e71
Source dataset
uspto-grants-2015_01
Patent number
US08933224B2

Reaction notes

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