Phosphorus oxychloride → HCID 59755129, compound

HRID 556413Notes

Reaction equation

HRID 556413 reaction equation
[CH2:1]([S:3][C:4]1[NH:5][C:6](=O)[C:7]2[S:12][C:11]3[N:13]=[C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:15]=[C:16]([CH3:17])[C:10]=3[C:8]=2[N:9]=1)[CH3:2].O=P(Cl)(Cl)[Cl:27].C(=O)([O-])O.[Na+]>>[Cl:27][C:6]1[C:7]2[S:12][C:11]3[N:13]=[C:14]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)[CH:15]=[C:16]([CH3:17])[C:10]=3[C:8]=2[N:9]=[C:4]([S:3][CH2:1][CH3:2])[N:5]=1

Participants

4

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 135427949HCID 135427949, compound

Product 1

HCID 59755129HCID 59755129, compoundYield 22.3%

Procedure

1.23 g (3.5 mmol) 2-ethylthio-9-methyl-7-phenyl-pyrido[3′,2′:4,5]-thieno[3,2-d]pyrimidin-4-one is refluxed in 10 ml (10.9 mol) phosphoroxychloride for 6 h. Then, the product is poured onto about 100 g ice water and neutralized with saturated sodium hydrogen carbonate solution. The precipitate is sucked off, washed with about 100 ml water, dried and purified by means of flash chromatography (dichloromethane/petroleum ether 5:1). 0.29 g (22%) 4-chloro-2-ethylthio-9-methyl-7-phenyl-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine is obtained.

Workup

  1. washwashed with about 100 ml water
  2. customdried
  3. custompurified by means of flash chromatography (dichloromethane/petroleum ether 5:1)

Sources & evidence

ORD record
ord-02786f04e14c419e9d03fa893b2e3af1
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Reaction notes

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