Chlorosuccinimide → 6-Chloro-2-propoxy-3-propylthieno[2,3-d]pyrimidin-4(3H)-one

HRID 1384859Notes

Reaction equation

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

Participants

Conditions

Temperature: 72.5 °C

Procedure

In a sulfonation flask, 10.1 g (0.04 mol) of 2-propoxy-3-propyl-3H-thieno[2.3-d]pyrimidin-4-one are added with stirring to 50 ml of absolute pyridine. The internal temperature is then raised to 70-75° C. and 9.0 g (0.07 mol) of N-chlorosuccinimid (NCS) are added over about 10 minutes in smallish portions. After stirring for 2 hours at 70-75° C., the pyridine is removed in a water-jet vacuum and the residue taken up in ethyl acetate. After washing twice with cold dilute aqueous hydrochloric acid, drying over sodium sulfate and removing the solvent in a water-jet vacuum, the crude product is obtained. The purification of the crude product is accomplished by column chromatography over silica gel (eluant: ethyl acetate/hexane=1:5), giving 7.8 g 6-chloro-2-propoxy-3-propyl-3H-thieno[2.3-d]pyrimidin-4-one in the form of a white powder having a melting point of 62-65° C.

Workup

customthe pyridine is removed in a water-jet vacuum
washAfter washing twice with cold dilute aqueous hydrochloric acid
dry with materialdrying over sodium sulfate
customremoving the solvent in a water-jet vacuum
customthe crude product is obtained
customThe purification of the crude product

Sources & evidence

ORD record: ord-fc7466f88f2249d7aa5d607a28450fd8
Source dataset: uspto-grants-2001_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06262058B1

Reaction notes

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