Hydrogen Peroxide → Pyrimidine-5-carboxamide

HRID 2036661Notes

Reaction equation

HRID 2036661 reaction equation
N[C:2]1[C:7]([C:8]#[N:9])=[C:6](N[C@H](C2N(C3C=NC=C(F)C=3)C3C=C(F)C=CC=3N=2)C)[N:5]=[CH:4][N:3]=1.C(=O)([O-])[O-:31].[K+].[K+].OO.O>CS(C)=O>[N:5]1[CH:6]=[C:7]([C:8]([NH2:9])=[O:31])[CH:2]=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 784Hydrogen PeroxideHCID 962WaterHCID 11430Potassium CarbonateHCID 58459115(S)-4-Amino-6-((1-(6-fluoro-1-(5-fluoropyridin-3-yl)-1H-benzo[d]imidazol-2-yl)ethyl)amino)pyrimidine-5-carbonitrile

Product 1

HCID 351819Pyrimidine-5-carboxamide

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

To a solution of (S)-4-amino-6-(1-(6-fluoro-1-(5-fluoropyridin-3-yl)-1H-benzo[d]imidazol-2-yl)ethylamino)pyrimidine-5-carbonitrile (0.040 g, 0.10 mmol) in DMSO (1.02 mL) was added potassium carbonate (0.017 g, 0.122 mmol) followed by hydrogen peroxide (31% in water, 0.635 mL, 6.42 mmol). After stirring for 2 h the solution was poured into water and extracted with EtOAc. Organic extracts were concentrated and purified by MPLC (eluted with 0-100% (1:10:90 NH4OH:MeOH:DCM) in DCM) to afford 4-amino-6-4(1S)-1-(6-fluoro-1-(5-fluoro-3-pyridinyl)-1H-benzimidazol-2-yl)ethyl)amino)-5-pyrimidinecarboxamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ ppm 1.51 (d, J=6.85 Hz, 3H) 5.34 (quin, J=6.94 Hz, 1H) 6.57 (s, 2H) 7.04-7.22 (m, 2H) 7.43 (br. s., 2H) 7.67-7.80 (m, 2H) 7.92 (d, J=7.63 Hz, 1H) 8.21 (dt, J=9.29, 2.10 Hz, 1H) 8.71 (s, 1H) 8.81 (d, J=2.74 Hz, 1H). LC-MS (ESI) m/z 411.0 [M+H]+.

Workup

  1. extractionextracted with EtOAc
  2. concentrationOrganic extracts were concentrated
  3. custompurified by MPLC (eluted with 0-100% (1:10:90 NH4OH:MeOH:DCM) in DCM)

Sources & evidence

ORD record
ord-310f31e57d114c13b5e0853fa4c47197
Source dataset
uspto-grants-2013_11
Patent number
US08575183B2

Reaction notes

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