Thiophene-3-methanol → HCID 10199524, compound

HRID 2264528Notes

Reaction equation

HRID 2264528 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]C[CH2:16][O:17][C:12]=3[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4](SC)[N:3]=1.CC(C)([O-])C.[K+].[OH:30][CH2:31][C:32]1[CH:36]=[CH:35][S:34][CH:33]=1>ClCCl>[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][CH2:16][O:17][C:12]=3[CH:11]=2)[C:5]([C:20]#[N:21])=[C:4]([O:30][CH2:31][C:32]2[CH:36]=[CH:35][S:34][CH:33]=2)[N:3]=1

Participants

5

Reactant 3

HCID 123570Thiophene-3-methanolHCID 17976008HCID 17976008, compoundHCID 23665647Potassium tert-butoxide

Product 1

HCID 10199524HCID 10199524, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
50 °C

Procedure

100 mg (0.26 mmol) of 2-amino-4-(2,3-dihydro-1,4-benzodioxin-6-yl)-6-(methylsulfanyl)-3,5-pyridinedicarbonitrile [prepared analogously to Dyachenko et al., Russian Journal of Chemistry, Vol. 33, No. 7, 1997, pages 1014-1017 or Vol. 34, No. 4, 1998, pages 557-563] are, together with 181 mg (1.6 mmol) of potassium tert-butoxide and 184 mg (1.6 mmol) of 3-hydroxymethylthiophene, stirred at 50° C. for 4 h. After cooling, the reaction mixture is diluted with dichloromethane and washed with water. The organic phase is dried with sodium sulfate and concentrated under reduced pressure. The residue is crystallized from diethyl ether.

Workup

  1. temperatureAfter cooling
  2. washwashed with water
  3. dry with materialThe organic phase is dried with sodium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customThe residue is crystallized from diethyl ether

Sources & evidence

ORD record
ord-cb7f8d82c50f41c68a5f4c82531ea34d
Source dataset
uspto-grants-2010_12
Patent number
US07855219B2

Reaction notes

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