Chlorosuccinimide → HCID 21183874, compound

HRID 1384852Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

In a sulfonation flask, 2.02 g (0.008 mol) of 2-propoxy-3-propylthieno[3.2-d]pyrimidin-4-one are added, with stirring, to 10 ml of absolute pyridine. The internal temperature is then raised to 70° C. and then 1.60 g (0.012 mol) of N-chlorosuccinimide (NCS) are added over about 5 min in smallish portions. After stirring for 1 hour at 70-75° C., the pyridine is removed in a water-jet vacuum and the residue is taken up in ethyl acetate. The mixture is washed repeatedly with dilute aqueous hydrochloric acid, dried over sodium sulfate and then the solvent is removed in the water-jet vacuum. The crude product so obtained is purified by column chromatography over silica gel (eluant: n-hexane/ethyl acetate=9:1), giving 2.2 g of 7-chloro-2-propoxy-3-propylthieno[3.4-d]pyrimidin-4-one in the form of a green powder having a melting point of 93-95° C.

Workup

customthe pyridine is removed in a water-jet vacuum
washThe mixture is washed repeatedly with dilute aqueous hydrochloric acid
dry with materialdried over sodium sulfate
customthe solvent is removed in the water-jet vacuum
customThe crude product so obtained
customis purified by column chromatography over silica gel (eluant: n-hexane/ethyl acetate=9:1)

Sources & evidence

ORD record: ord-3baa9a672ece449db82aa5f6400b5429
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262058B1

Reaction notes

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