Cesium carbonate → HCID 117678140, compound

HRID 1427367Notes

Reaction equation

HRID 1427367 reaction equation
OC1C2CN(C(OCC3C=CC=CC=3)=O)CCC=2N=C(C)N=1.ClC(F)(F)C([O-])=O.[Na+].C(=O)([O-])[O-].[Cs+].[Cs+].[F:37][CH:38]([F:61])[O:39][C:40]1[C:41]2[CH2:50][N:49](C(OCC3C=CC=CC=3)=O)[CH2:48][CH2:47][C:42]=2[N:43]=[C:44]([CH3:46])[N:45]=1>>[F:61][CH:38]([F:37])[O:39][C:40]1[C:41]2[CH2:50][NH:49][CH2:48][CH2:47][C:42]=2[N:43]=[C:44]([CH3:46])[N:45]=1

Participants

5

Reactant 4

HCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 117678330HCID 117678330, compoundHCID 178433417HCID 178433417, compound

Product 1

HCID 117678140HCID 117678140, compound

Procedure

Benzyl 4-hydroxy-2-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate (see footnote 8) was reacted with sodium chloro(difluoro)acetate and cesium carbonate to generate benzyl 4-(difluoromethoxy)-2-methyl-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate; hydrogenolytic removal of the protecting group provided the requisite 4-(difluoromethoxy)-2-methyl-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine.

Workup

  1. customhydrogenolytic removal of the protecting group

Sources & evidence

ORD record
ord-4f34a3a2f94b467b8201ae1324cd2ba9
Source dataset
uspto-grants-2015_01
Patent number
US08933224B2

Reaction notes

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