Methyl iodide → N-(2,5-Dimethyl-1H-pyrrol-1-yl)-N-methyl-6-(morpholin-4-yl)pyridazin-3-amine

HRID 1390005Notes

Reaction equation

[CH3:1][C:2]1[N:3]([NH:8][C:9]2[N:10]=[N:11][C:12]([N:15]3[CH2:20][CH2:19][O:18][CH2:17][CH2:16]3)=[CH:13][CH:14]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1.[H-].[Na+].[CH3:23]I>CN(C)C=O>[CH3:1][C:2]1[N:3]([N:8]([CH3:23])[C:9]2[N:10]=[N:11][C:12]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:13][CH:14]=2)[C:4]([CH3:7])=[CH:5][CH:6]=1

Participants

Conditions

Temperature: 55 °C

Procedure

To 1.36 g (5 m moles) of N-(2,5-dimethyl-1H-pyrrol-1-yl)-6-morpholino-3-pyridazineamine in 13.6 ml of dimethylformamide, 0.26 g (5.5 m moles) of 55% sodium hydride are added. The mixture is stirred for 30 minutes at room temperature and for additional 30 minutes at 55° C. Then, a solution of 0.78 g (5.5 m moles) of methyl iodide in 2 ml of dimethylformamide is gradually added at 10° C. When the addition is completed the mixture is heated at 50° C. for 45 minutes. The dimethylformamide is evaporated off in vacuo and the residue is dissolved in ethyl acetate. The organic layer is washed with water and then evaporated to dryness to give a solid which is crystallized from hexane. Yield 0.7 g (54%) of the product of the title which melts at 119°-122° C.

Workup

additionWhen the addition
temperatureis heated at 50° C. for 45 minutes
customThe dimethylformamide is evaporated off in vacuo
dissolutionthe residue is dissolved in ethyl acetate
washThe organic layer is washed with water
customevaporated to dryness
customto give a solid which
customis crystallized from hexane

Sources & evidence

ORD record: ord-8dca016210da465d88058a16d9cb86a8
Source dataset: uspto-grants-1981_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04247551

Reaction notes

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