Methylboronic Acid → HCID 71778129, compound

HRID 1427368Notes

Reaction equation

HRID 1427368 reaction equation
ClC1C2CN(C(OCC3C=CC=CC=3)=O)CCC=2N=C(C)N=1.CB(O)O.[CH3:27][C:28]1[N:29]=[C:30]([CH3:48])[C:31]2[CH2:37][N:36](C(OCC3C=CC=CC=3)=O)[CH2:35][CH2:34][C:32]=2[N:33]=1>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:27][C:28]1[N:29]=[C:30]([CH3:48])[C:31]2[CH2:37][NH:36][CH2:35][CH2:34][C:32]=2[N:33]=1

Participants

5

Reactant 3

HCID 139377Methylboronic AcidHCID 117678246HCID 117678246, compoundHCID 117678406HCID 117678406, compound

Product 1

HCID 71778129HCID 71778129, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Procedure

Benzyl 4-chloro-2-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (see footnote 8) was reacted with methylboronic acid and [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) to generate benzyl 2,4-dimethyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate; hydrogenolytic removal of the protecting group provided the requisite 2,4-dimethyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine.

Workup

  1. customhydrogenolytic removal of the protecting group

Sources & evidence

ORD record
ord-d885c6f4105e4a759c5499079cc2e6d4
Source dataset
uspto-grants-2015_01
Patent number
US08933224B2

Reaction notes

Loading…