Hydrochloric Acid → HCID 86653538, compound

HRID 1428182Notes

Reaction equation

HRID 1428182 reaction equation
[C:1](#[N:5])[CH2:2][C:3]#[N:4].[H-].[Na+].Cl[C:9]1[CH:14]=[C:13]([Cl:15])[N:12]=[C:11]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:10]=1.[OH-].[Na+].Cl>C1COCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:15][C:13]1[N:12]=[C:11]([N:16]2[CH2:21][CH2:20][O:19][CH2:18][CH2:17]2)[N:10]=[C:9]([CH:2]([C:1]#[N:5])[C:3]#[N:4])[CH:14]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 8010MalononitrileHCID 14798Sodium HydroxideHCID 24758Sodium hydrideHCID 27720684-(4,6-Dichloropyrimidin-2-yl)morpholine

Product 1

HCID 86653538HCID 86653538, compoundYield 111.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of malononitrile (277 mg, 4.2 mmol) in THF cooled to 0° C., sodium hydride (189 mg, 4.7 mmol) was added. When the evolution of gas ceased, 4,6-dichloro-2-morpholinopyrimidine (1aa) (500 mg, 2.1 mmol) was added to the reaction mixture, followed by Pd(PPh3)4. The resulting suspension was refluxed at 80° C. overnight. The mixture was treated with aq. 2M NaOH (10 mL) and stirred for 15 min. The organic layer was discharged and the aqueous was acidified with aq. 2M HCl and extracted with ethyl acetate, yielding 2-(6-chloro-2-morpholinopyrimidin-4-yl)malononitrile (2aa) (617 mg) after drying and solvent evaporation.

Workup

  1. extractionextracted with ethyl acetate

Sources & evidence

ORD record
ord-121c543a287b46febefb116de9635571
Source dataset
uspto-grants-2015_01
Patent number
US08937064B2

Reaction notes

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