Potassium Carbonate → 5-((3R,4R)-3-aminotetrahydro-2H-pyran-4-ylamino)-3-(p-tolylamino)pyrazine-2-carboxamide

HRID 332823Notes

Reaction equation

HRID 332823 reaction equation
[NH2:1][C@@H:2]1[C@H:7]([NH:8][C:9]2[N:10]=[C:11]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)[C:12]([C:15]#[N:16])=[N:13][CH:14]=2)[CH2:6][CH2:5][O:4][CH2:3]1.C([O-])([O-])=[O:26].[K+].[K+]>CO.OO>[NH2:1][C@@H:2]1[C@H:7]([NH:8][C:9]2[N:10]=[C:11]([NH:17][C:18]3[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][CH:19]=3)[C:12]([C:15]([NH2:16])=[O:26])=[N:13][CH:14]=2)[CH2:6][CH2:5][O:4][CH2:3]1

Participants

5

Reactant 2

HCID 11430Potassium CarbonateHCID 866856155-((3R,4R)-3-aminotetrahydro-2H-pyran-4-ylamino)-3-(p-tolylamino)pyrazine-2-carbonitrile

Product 1

HCID 866856165-((3R,4R)-3-aminotetrahydro-2H-pyran-4-ylamino)-3-(p-tolylamino)pyrazine-2-carboxamide

Reagents, catalysts & solvents 2

HCID 784Hydrogen PeroxideCatalystHCID 887MethanolSolvent

Procedure

To a solution of 5-((3R,4R)-3-aminotetrahydro-2H-pyran-4-ylamino)-3-(p-tolylamino)pyrazine-2-carbonitrile in methanol (1 ml) was added K2CO3 (excess) and H2O2 (50%, a few drops). After completion, it was concentrated and purified by preparative HPLC to give 5-((3R,4R)-3-aminotetrahydro-2H-pyran-4-ylamino)-3-(p-tolylamino)pyrazine-2-carboxamide. MS found for C17H22N6O2 as (M+H)+ 343.3, UV: λ=251.2, 302.9.

Workup

  1. concentrationAfter completion, it was concentrated
  2. custompurified by preparative HPLC

Sources & evidence

ORD record
ord-bece9f55e56b40569de315a5666eda82
Source dataset
uspto-grants-2014_11
Patent number
US08877760B2

Reaction notes

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