Ammonia → 7-(3,4-Dimethoxyphenyl)-9-methyl-pyrido[3',2':4,5]thieno[3,2-d]pyrimidine-2,4-dione

HRID 556406Notes

Reaction equation

HRID 556406 reaction equation
[NH2:1][C:2]1[C:10]2[C:5](=[N:6][C:7]([C:12]3[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[C:14]([O:20][CH3:21])[CH:13]=3)=[CH:8][C:9]=2[CH3:11])[S:4][C:3]=1[C:22]([NH2:24])=[O:23].Cl[C:26]([O:29]C(Cl)=O)(Cl)Cl.N>O1CCOCC1.O>[CH3:21][O:20][C:14]1[CH:13]=[C:12]([C:7]2[CH:8]=[C:9]([CH3:11])[C:10]3[C:2]4[NH:1][C:26](=[O:29])[NH:24][C:22](=[O:23])[C:3]=4[S:4][C:5]=3[N:6]=2)[CH:17]=[CH:16][C:15]=1[O:18][CH3:19]

Participants

6

Reactant 3

HCID 222AmmoniaHCID 10426DiphosgeneHCID 575037143-Amino-6-(3,4-dimethoxyphenyl)-4-methyl-thieno[2,3-b]pyridine-2-carboxamide

Product 1

HCID 115887347-(3,4-Dimethoxyphenyl)-9-methyl-pyrido[3',2':4,5]thieno[3,2-d]pyrimidine-2,4-dioneYield 96%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

3.0 g (8.7 mmol) 3-amino-6-(3,4-dimethoxyphenyl)-4-methyl-thieno[2,3-b]pyridine-2-carboxamide is suspended in 100 ml absolute dioxane. Then, 1.1 ml (8.7 mmol) chloroformic acid trichloromethylester (diphosgene) is added and refluxed for 3 h. Following cooling, the precipitate is sucked off and then suspended in 50 ml water. The suspension is adjusted to pH 8 using concentrated ammonia solution and the precipitate is sucked off, washed with some water, suck dried and in vacuo at 50° C. 3.08 g (96%) 7-(3,4-dimethoxyphenyl)-9-methyl-pyrido[3′,2′:4,5]thieno[3,2-d]pyrimidine-2,4-dione is obtained.

Workup

  1. temperaturerefluxed for 3 h
  2. temperatureFollowing cooling
  3. washwashed with some water, suck
  4. customdried and in vacuo at 50° C

Sources & evidence

ORD record
ord-85dccb1e3e684613b44186e4fb3f39fa
Source dataset
uspto-grants-2011_11
Patent number
US08058285B2

Reaction notes

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