Chlorosuccinimide → 2-n-butyl-6-chloro-3-n-propyl-3H-thieno[2,3-d]pyrimidine-4-one

HRID 650935Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

In a sulfonation flask, 2.0 g (8 mmol) of 2-n-butyl-3-propyl-3H-thieno[2.3-d]pyrimidin-4-one are added, with stirring, to 15 ml of absolute pyridine. The internal temperature is then raised to 80° C. and then 1.87 g (14 mmol) of N-chlorosuccinimide (NCS) are added in smallish portions. After stirring for 3 hours at 90° C. 1.0 g of NCS is added and the mixture is stirred another 3 hours at 90° C. The pyridine is removed in a water-jet vacuum and the crude product so obtained is purified by column chromatography over silica gel (eluant:n-hexane/tert.butylmethylether=3:1), giving 0.9 g of 2-n-butyl-6-chloro-3-propyl-3H-thieno-[2.3-d]pyrimidin-4-one in the form of a beige powder having a melting point of 67-69° C.

Workup

stirringthe mixture is stirred another 3 hours at 90° C
customThe pyridine is removed in a water-jet vacuum
customthe crude product so obtained
customis purified by column chromatography over silica gel (eluant:n-hexane/tert.butylmethylether=3:1)

Sources & evidence

ORD record: ord-6135ac5f36c34adabbb644a1a3a3525e
Source dataset: uspto-grants-2001_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06277858B1

Reaction notes

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