Ethanol → HCID 86655330, compound

HRID 877006Notes

Reaction equation

HRID 877006 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[N:15]=[C:14]([N:16]3[CH2:20][CH2:19][CH2:18][C:17]3=[O:21])[CH:13]=[CH:12][CH:11]=2)[C:5]([NH2:22])=[C:4]([Cl:23])[N:3]=1.CCO.[N:27]([O-])=O.[Na+]>C(O)(=O)C.O>[NH2:1][C:2]1[N:3]=[C:4]([Cl:23])[C:5]2[N:22]=[N:27][N:8]([CH2:9][C:10]3[N:15]=[C:14]([N:16]4[CH2:20][CH2:19][CH2:18][C:17]4=[O:21])[CH:13]=[CH:12][CH:11]=3)[C:6]=2[N:7]=1

Participants

6

Reactant 3

HCID 702EthanolHCID 23668193Sodium NitriteHCID 86655329HCID 86655329, compound

Product 1

HCID 86655330HCID 86655330, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent

Procedure

A suspension of 1-{6-[(2,5-diamino-6-chloro-pyrimidin-4-ylamino)methyl]pyridin-2-yl}pyrrolidin-2-one (2.10 g, 6.29 mmol) in glacial acetic acid mL) and EtOH (24 mL) at 0° C. was treated with a solution of sodium nitrite (0.564 g, 8.17 mmol) in water (1.5 mL), stirred for 2 h, warmed to room temperature and the resulting precipitate filtered and dried to give the title compound (1.67 g, 77%) as an off-white solid; LC-MS retention time 1.99 min, (M+H)+ 345.

Workup

  1. filtrationthe resulting precipitate filtered
  2. customdried

Sources & evidence

ORD record
ord-6b7339948b6b479ab0e9bdf67cad7071
Source dataset
uspto-grants-2015_03
Patent number
US08987279B2

Reaction notes

Loading…