Sodium hydride → 6-Cyclopropylmethoxy-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine

HRID 657861Notes

Reaction equation

[CH:1]1([CH2:4][OH:5])[CH2:3][CH2:2]1.[H-].[Na+].Br.Cl[C:10]1[CH:11]=[C:12]([CH3:20])[C:13]2[N:14]([C:16]([NH2:19])=[N:17][N:18]=2)[N:15]=1>CN(C=O)C>[CH:1]1([CH2:4][O:5][C:10]2[CH:11]=[C:12]([CH3:20])[C:13]3[N:14]([C:16]([NH2:19])=[N:17][N:18]=3)[N:15]=2)[CH2:3][CH2:2]1

Participants

Conditions

Temperature: 50 °C

Procedure

Cyclopropylmethanol (2.99 ml) was initially charged in DMF (30 ml), admixed under argon with sodium hydride (907 mg) and stirred at 50° C. for 1 h. Subsequently, 6-chloro-8-methyl-[1,2,4]triazolo[4,3-b]pyridazin-3-ylamine hydrobromide (W2.002; 2.0 g) were dissolved in DMF (30 ml) and one equivalent of the alkoxide solution was added. After stirring at 50° C. for one hour, two further equivalents of alkoxide solution were added and the mixture was stirred further at 50° C. The reaction mixture was then dried and purified using silica gel (80 g cartridge, dichloromethane/methanol gradient of 0-10% in 40 min). 620 mg of the title compound were obtained. LC-MS rt: 0.57 min [M+H]+: 220.1 (met. b)

Workup

stirringAfter stirring at 50° C. for one hour
stirringthe mixture was stirred further at 50° C
customThe reaction mixture was then dried
custompurified
customsilica gel (80 g cartridge, dichloromethane/methanol gradient of 0-10% in 40 min)

Sources & evidence

ORD record: ord-ba033cc4e6c140c1914b60865066082e
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08076336B2

Reaction notes

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