Water → HCID 135847203, compound

HRID 1607886Notes

Reaction equation

HRID 1607886 reaction equation
[H-].[Al+3].[Li+].[H-].[H-].[H-].[C:7]([C:11]1[CH:16]=[C:15]([NH:17][C:18]2[CH:23]=[N:22][C:21]([C:24](OC)=[O:25])=[CH:20][N:19]=2)[CH:14]=[C:13]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:12]=1[OH:32])([CH3:10])([CH3:9])[CH3:8].O.S([O-])([O-])(=O)=O.[Mg+2]>C(OCC)C.O1CCCC1>[C:7]([C:11]1[CH:16]=[C:15]([NH:17][C:18]2[CH:23]=[N:22][C:21]([CH2:24][OH:25])=[CH:20][N:19]=2)[CH:14]=[C:13]([C:28]([CH3:31])([CH3:30])[CH3:29])[C:12]=1[OH:32])([CH3:10])([CH3:9])[CH3:8]

Participants

7

Reactant 4

HCID 962WaterHCID 24083Sulfuric acid magnesium salt (1:1)HCID 21226445Aluminium lithium hydrideHCID 136094458HCID 136094458, compound

Product 1

HCID 135847203HCID 135847203, compoundYield 65.1%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium aluminum hydride (0.14 g) was suspended in 26 ml of diethyl ether. While the suspension was stirred at room temperature, 13 ml of a solution of 0.50 g of 2,6-di-tert-butyl-4-[(5-methoxycarbonyl-2-pyrazinyl)amino]phenol (Compound20) in tetrahydrofuran was added thereto. The resulting mixture was furtherstirred at room temperature for 4 hours. With cooling on an ice bath 0.5 mlof water was added thereto, followed by addition of 1.4 g of magnesium sulfate, and the mixture was stirred for 15 minutes. Insoluble materials were filtered off, and the filtrate was concentrated. The resulting crude product was purified by silica gel column chromatography (eluent: methanol-chloroform=1:19), giving 0.30 g of the title compound (Compound 32) as a pale yellow solid.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 15 minutes
  3. filtrationInsoluble materials were filtered off
  4. concentrationthe filtrate was concentrated
  5. customThe resulting crude product was purified by silica gel column chromatography (eluent: methanol-chloroform=1:19)

Sources & evidence

ORD record
ord-ad2b0c88aa174e7da00bd44c877e395e
Source dataset
uspto-grants-1989_09
Patent number
US04868183

Reaction notes

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