Ethanol → HCID 90408828, compound

HRID 2177628Notes

Reaction equation

HRID 2177628 reaction equation
[F:1][C:2]1[CH:3]=[N:4][C:5]([NH2:8])=[N:6][CH:7]=1.[H-].[Na+].[Cl:11][C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[C:16](Cl)[CH:15]=[C:14]([CH3:22])[N:13]=1.C(O)C>C1COCC1.CCOC(C)=O.CCCCCC>[Cl:11][C:12]1[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([NH:8][C:5]2[N:6]=[CH:7][C:2]([F:1])=[CH:3][N:4]=2)[CH:15]=[C:14]([CH3:22])[N:13]=1

Participants

8

Reactant 4

HCID 702EthanolHCID 24758Sodium hydrideHCID 27848192,4-Dichloro-6-methyl-3-nitropyridineHCID 152096945-Fluoropyrimidin-2-amine

Product 1

HCID 90408828HCID 90408828, compoundYield 63%

Reagents, catalysts & solvents 3

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a mixture of 5-fluoropyrimidin-2-amine (8.2 g, 72.1 mmol) and sodium hydride (5.8 g, 144 mmol) in THF (100 mL) was added 2,4-dichloro-6-methyl-3-nitropyridine (15 g, 72.1 mmol). After stirring for 10 h, ethanol was added. Silica gel chromatography (5:1 Hexane:EtOAc) provided the product as a yellow solid (12.8 g, 63%).

Sources & evidence

ORD record
ord-5076d506ecf84dde84f5327aa15247cc
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

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