Dimethylformamide → (3-Propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene)methylamine

HRID 1167142Notes

Reaction equation

HRID 1167142 reaction equation
[CH2:1]([N:4]1[C:9](=N)[C:8]2[CH:11]=[CH:12][S:13][C:7]=2[N:6]=[C:5]1[O:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH3:3].CI.C(=O)([O-])[O-].[K+].[K+].[CH3:26][N:27](C=O)C>>[CH2:1]([N:4]1[C:9](=[CH:26][NH2:27])[C:8]2[CH:11]=[CH:12][S:13][C:7]=2[N:6]=[C:5]1[O:14][CH2:15][CH2:16][CH3:17])[CH2:2][CH3:3]

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 229958193-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene amine

Product 1

HCID 69986416(3-Propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene)methylamine

Procedure

In a sulfonation flask 4.5 g (0.018 mol) 3-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene amine, 5.1 g (0.036 mol) CH3I, 5.0 g (0.036 mol) powdered potassium carbonate and 80 ml of absolute DMF are stirred for 4 hours at an internal temperature of 90-100° C. Then the solvent is distilled off in vacuum, the residue taken up in ethylacetate and the organic phase twice washed with water. After drying the organic phase over Na2SO4 the ethylacetate is distilled off in a water jet vacuum and the residue purified by column chromatography over silica gel (eluant: hexane/ethylacetate 1:6). Yield: 4.4 g of (3-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene)methylamine in the form of a brown oil.

Workup

  1. distillationThen the solvent is distilled off in vacuum
  2. washthe organic phase twice washed with water
  3. dry with materialAfter drying the organic phase over Na2SO4 the ethylacetate
  4. distillationis distilled off in a water jet vacuum
  5. customthe residue purified by column chromatography over silica gel (eluant: hexane/ethylacetate 1:6)

Sources & evidence

ORD record
ord-ad9813d6fb9a49c299a7c49a782ff21a
Source dataset
uspto-grants-2003_09
Patent number
US06617330B2

Reaction notes

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