N-bromobutanimide → (6-Bromo-3-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene)methylamine

HRID 1167143Notes

Reaction equation

[CH2:1]([N:4]1[C:9](=[CH:10][NH2:11])[C:8]2[CH:12]=[CH:13][S:14][C:7]=2[N:6]=[C:5]1[O:15][CH2:16][CH2:17][CH3:18])[CH2:2][CH3:3].[Br:19]N1C(=O)CCC1=O>N1C=CC=CC=1>[Br:19][C:13]1[S:14][C:7]2[N:6]=[C:5]([O:15][CH2:16][CH2:17][CH3:18])[N:4]([CH2:1][CH2:2][CH3:3])[C:9](=[CH:10][NH2:11])[C:8]=2[CH:12]=1

Participants

Conditions

Temperature: 60 °C

Procedure

In a sulfonation flask, 1.2 g (0.0045 mol) (3-propyl-2-propoxy-3H-thieno[2,3-d]-pyrimidine-4-ylidene)methylamine are dissolved in 15 ml of absolute pyridine. Then the internal temperature is raised to 60° C. and 1.2 g (0.0068 mol) N-bromosuccinimide are added in three portions. After stirring for 3 hours at 60° C., the pyridine is distilled off in a water jet vacuum and the residue taken up in ethylacetate. The organic phase is washed three times 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/ethylacetate 3:1). Yield: 1.2 g of (6-bromo-3-propyl-2-propoxy-3H-thieno[2,3-d]pyrimidine-4-ylidene)methylamine in the form of a brownish oil (1H-NMR-data see table 5).

Workup

distillationthe pyridine is distilled off in a water jet vacuum
washThe organic phase is washed three times with water
dry with materialafter drying the organic phase over Na2SO4 the solvent
customis removed in a water jet vacuum
customThe raw material is purified by column chromatography over silica gel (eluant: hexane/ethylacetate 3:1)

Sources & evidence

ORD record: ord-6c87a49ec6c3405fb0de550efd01e9a1
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06617330B2

Reaction notes

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