(2-Methyl-1,3-thiazol-4-yl)methanol → 2-Amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-[(2-methyl-1,3-thiazol-4-yl)-methoxy]-3,5-pyridinedicarbonitrile

HRID 2264527Notes

Reaction equation

HRID 2264527 reaction equation
[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:19]=[CH:18][C:13]3[O:14][CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4](SC2C=CC=CC=2)[N:3]=1.CC(C)([O-])C.[K+].[CH3:35][C:36]1[S:37][CH:38]=[C:39]([CH2:41][OH:42])[N:40]=1>COCCOC>[NH2:1][C:2]1[C:7]([C:8]#[N:9])=[C:6]([C:10]2[CH:19]=[CH:18][C:13]3[O:14][CH2:15][CH2:16][O:17][C:12]=3[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([O:42][CH2:41][C:39]2[N:40]=[C:36]([CH3:35])[S:37][CH:38]=2)[N:3]=1

Participants

5

Reactant 3

HCID 10582809(2-Methyl-1,3-thiazol-4-yl)methanolHCID 179760052-Amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 101581582-Amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-[(2-methyl-1,3-thiazol-4-yl)-methoxy]-3,5-pyridinedicarbonitrile

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

100 mg (0.26 mmol) of 2-amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-(phenylsulfanyl)-3,5-pyridinedicarbonitrile [prepared analogously to Kambe et al., Synthesis, 531-533 (1981)] are, together with 44 mg (0.39 mmol) of potassium tert-butoxide and 334 mg (2.59 mmol) of (2-methyl-1,3-thiazol-4-yl)methyl alcohol, stirred in 5 ml of 1,2-dimethoxyethane at room temperature overnight. The reaction solution is concentrated under reduced pressure and the residue is then purified by preparative HPLC on reversed-phase silica gel.

Workup

  1. concentrationThe reaction solution is concentrated under reduced pressure
  2. customthe residue is then purified by preparative HPLC on reversed-phase silica gel

Sources & evidence

ORD record
ord-fc34d274ab024ac089b949f4b29fd60b
Source dataset
uspto-grants-2010_12
Patent number
US07855219B2

Reaction notes

Loading…