Propylamine → 3-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene amine

HRID 1167141Notes

Reaction equation

HRID 1167141 reaction equation
[C:1]([C:3]1[CH:7]=[CH:6][S:5][C:4]=1[N:8]=[C:9]([O:14][CH2:15][CH2:16][CH3:17])OCCC)#[N:2].[NH2:18][CH2:19][CH2:20][CH3:21]>>[CH2:19]([N:18]1[C:1](=[NH:2])[C:3]2[CH:7]=[CH:6][S:5][C:4]=2[N:8]=[C:9]1[O:14][CH2:15][CH2:16][CH3:17])[CH2:20][CH3:21]

Participants

3

Reactant 2

HCID 7852PropylamineHCID 229958273-Cyano-2-(1,1-dipropoxymethylenamino) thiophene

Product 1

HCID 229958193-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene amine

Procedure

In a sulfonation flask, 5.7 g (0.023 mol) 3-cyano-2-(1,1-dipropoxymethylenamino)thiophene and 35 ml 1-aminopropane are heated at reflux temperature for 5 hours. Then the excess of 1-aminopropane is distilled off and the residue purified by column chromatography over silica gel (eluant: hexane/ethylacetate 1:1). Yield: 5.1 g of 3-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylideneamine in the form of brownish crystals; m.p. 61-63° C.

Workup

  1. temperatureat reflux temperature for 5 hours
  2. distillationThen the excess of 1-aminopropane is distilled off
  3. customthe residue purified by column chromatography over silica gel (eluant: hexane/ethylacetate 1:1)

Sources & evidence

ORD record
ord-373930ff689d4945886d57a8d43ea257
Source dataset
uspto-grants-2003_09
Patent number
US06617330B2

Reaction notes

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