Dimethylformamide → HCID 69986120, compound

HRID 1167137Notes

Reaction equation

HRID 1167137 reaction equation
[CH2:1]([C:5]1[N:6]([CH2:15][CH2:16][CH3:17])[C:7](=N)[C:8]2[CH:13]=[CH:12][S:11][C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4].C(=O)([O-])[O-].[Na+].[Na+].[CH3:24][N:25](C=O)C>>[CH2:1]([C:5]1[N:6]([CH2:15][CH2:16][CH3:17])[C:7](=[CH:24][NH2:25])[C:8]2[CH:13]=[CH:12][S:11][C:9]=2[N:10]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 10340Sodium CarbonateHCID 59042613HCID 59042613, compound

Product 1

HCID 69986120HCID 69986120, compound

Procedure

In a sulfonation flask 3.74 g (0.015 mol) 2-butyl-3-propyl-3H-thieno [2,3-d]pyrimidine-4-ylideneamine, 2.84 g (0.03 mol) Mel, 4.15 g (0.03 mol) powdered sodium carbonate and 50 ml abs. DMF are stirred for 4 hours at an internal temperature of 70° C. Then DMF is distilled off in vacuum and the residue taken up in ethylacetate. The organic phase is washed with water and after drying the organic phase over Na2SO4 the solvent is removed in a water jet vacuum. The raw material is purified by column chromatography over silica gel (eluant: hexane/THF 1:1). Yield: 2.7 g of (2-butyl-3-propyl-3H-thieno [2,3-d]pyrimidin-4-ylidene) methylamine in the form of yellow crystals, m.p. 45-47° C.

Workup

  1. distillationThen DMF is distilled off in vacuum
  2. washThe organic phase is washed with water
  3. dry with materialafter drying the organic phase over Na2SO4 the solvent
  4. customis removed in a water jet vacuum
  5. customThe raw material is purified by column chromatography over silica gel (eluant: hexane/THF 1:1)

Sources & evidence

ORD record
ord-0cc91c6860a3495b937a1fcc1703d2ab
Source dataset
uspto-grants-2003_09
Patent number
US06617330B2

Reaction notes

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