Isopropylamine → HCID 86703043, compound

HRID 1851229Notes

Reaction equation

[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6](Cl)[N:5]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:17]=[C:4]2[N:3]=1.[CH:24]([NH2:27])([CH3:26])[CH3:25]>CN(C=O)C>[Cl:1][C:2]1[C:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[C:6]([NH:27][CH:24]([CH3:26])[CH3:25])[N:5]2[N:15]=[C:16]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][N:19]=3)[N:17]=[C:4]2[N:3]=1

Participants

Conditions

Temperature: 100 °C

Procedure

1 g (2.9 mmol) 5,7-dichloro-6-phenyl-2-pyridine-2-yl-[1,2,4]triazolo[1,5-a]pyrimidine described in the former example are given in 10 mL DMF (no complete dissolution). After addition of 0.62 mL (7.3 mmol) isopropylamine the reaction mixture is heated in a microwave oven at 100° C. for 20 minutes. From the clear brown solution the DMF is evaporated, the residue is diluted with brine and water and extracted three times with dichloromethane. The combined organic extracts are dried over Na2SO4 and the solvent is evaporated. The reaction is repeated twice with 1 g starting material resp. 200 mg. The crude residues after the work-up are combined and purified jointly by chromatography (silicagel, eluents: dichloromethane, methanol) yielding 856.1 mg (36.5%) of the desired product.

Workup

dissolutionno complete dissolution)
customFrom the clear brown solution the DMF is evaporated
additionthe residue is diluted with brine and water
extractionextracted three times with dichloromethane
dry with materialThe combined organic extracts are dried over Na2SO4
customthe solvent is evaporated
custompurified jointly by chromatography (silicagel, eluents: dichloromethane, methanol)

Sources & evidence

ORD record: ord-00bd6988ebbb4f479c3f25c898d6e59a
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08957064B2

Reaction notes

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