2-Chloropyrimidine → HCID 10065515, compound

HRID 241811Notes

Reaction equation

HRID 241811 reaction equation
[NH2:1][C:2]1[C:6]2=[N:7][N:8]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=3)[C:9](=[O:11])[CH:10]=[C:5]2[NH:4][N:3]=1.Cl[C:21]1[N:26]=[CH:25][CH:24]=[CH:23][N:22]=1>CN1CCCC1=O.CO>[CH3:19][O:18][C:15]1[CH:16]=[CH:17][C:12]([N:8]2[C:9](=[O:11])[CH:10]=[C:5]3[NH:4][N:3]=[C:2]([NH:1][C:21]4[N:26]=[CH:25][CH:24]=[CH:23][N:22]=4)[C:6]3=[N:7]2)=[CH:13][CH:14]=1

Participants

5

Reactant 2

HCID 744042-ChloropyrimidineHCID 6413030HCID 6413030, compound

Product 1

HCID 10065515HCID 10065515, compoundYield 56.6%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
130 °C

Procedure

To 3-amino-5-(4-methoxy-phenyl)-1,5-dihydro-pyrazolo[4,3-c]pyridazin-6-one (purchased from Bionet, 67.6 mg, 0.2628 mmoles) in N-methylpyrrolidinone (263 uL) was added 2-chloro-pyrimidine (15.1 mg, 0.5 eq). The reaction was stirred for 5 hours at 130° C. to give crude desired product as evidenced by mass spectrometry. The reaction was diluted with methanol (2 ml) and purified by reverse phase chromatography to give 25 mg (28%) of pure 5-(4-methoxy-phenyl)-3-(pyrimidin-2-ylamino)-1,5-dihydro-pyrazolo[4,3-c]pyridazin-6-one (I-17) as a solid. LC/MS: tret=2.13 min, M+H−=336.1.

Workup

  1. customto give crude desired product
  2. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-cf988856333643b58846a4f1e9c25c75
Source dataset
uspto-grants-2014_02
Patent number
US08653088B2

Reaction notes

Loading…