Tetrahydrofuran → HCID 21912290, compound

HRID 2307968Notes

Reaction equation

HRID 2307968 reaction equation
[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:20]([CH3:21])=[CH:19][C:18]([CH2:22][OH:23])=[CH:17][C:16]=2[CH3:24])[C:8]=1[CH3:25])[CH2:4][CH3:5])[CH3:2].[OH-].[Na+].[CH2:28]1COCC1>>[CH2:1]([CH:3]([NH:6][C:7]1[CH:12]=[C:11]([CH3:13])[N:10]=[C:9]([O:14][C:15]2[C:16]([CH3:24])=[CH:17][C:18]([CH2:22][O:23][CH3:28])=[CH:19][C:20]=2[CH3:21])[C:8]=1[CH3:25])[CH2:4][CH3:5])[CH3:2]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 14798Sodium HydroxideHCID 69587603HCID 69587603, compound

Product 1

HCID 21912290HCID 21912290, compound

Procedure

To a solution of {4-[4-(1-Ethyl-propylamino)-3,6-dimethyl-pyridin-2-yloxy]-3,5-dimethyl-phenyl}-methanol in dry THF was added 60% NaOH in oil and stirred for 5 min. Excess of Mel was added and stirred at room temperature for 2 hr. After standard worked up procedure and purification, the title compound was obtained as a clear golden oil. 1H NMR(CDCl3) d 7.02(s,2H), 6.06(s,1H), 4.40(s,3H), 3.72(d,1H), 3.39(s,3H), 3.36(m,1H), 2.12(s,3H), 2.11(s,3H), 2.10(s,6H), 1.4-1.7(m,4H), 0.95(t,6H) ppm.

Workup

  1. additionExcess of Mel was added
  2. stirringstirred at room temperature for 2 hr
  3. customprocedure and purification

Sources & evidence

ORD record
ord-cfb45af95f9d42a1adb7ecd746b021a1
Source dataset
uspto-grants-2004_12
Patent number
US06833378B2

Reaction notes

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