Trifluoroacetic acid → 3-(6-(2-mercaptoethyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

HRID 2201289

反応式

HRID 2201289 の反応式
[CH3:1][N:2]1[C:7]2=[CH:8][N:9]([CH2:19][CH2:20][S:21]C(C3C=CC=CC=3)(C3C=CC=CC=3)C3C=CC=CC=3)[C:10]([C:11]3[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=3)[C:14]#[N:15])=[C:6]2[C:5](=[O:41])[N:4]([CH3:42])[C:3]1=[O:43].CSC1NC(=S)NC(=S)N=1.C([SiH](CC)CC)C.C(O)(C(F)(F)F)=O>C(Cl)Cl>[SH:21][CH2:20][CH2:19][N:9]1[C:10]([C:11]2[CH:12]=[C:13]([CH:16]=[CH:17][CH:18]=2)[C:14]#[N:15])=[C:6]2[C:7]([N:2]([CH3:1])[C:3](=[O:43])[N:4]([CH3:42])[C:5]2=[O:41])=[CH:8]1

参加物

6

反応物 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 12210973Si-TMTHCID 867235233-(1,3-Dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

生成物 1

HCID 867234173-(6-(2-mercaptoethyl)-1,3-dimethyl-2,4-dioxo-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

3-(1,3-Dimethyl-2,4-dioxo-6-(2-(tritylthio)ethyl)-2,3,4,6-tetrahydro-1H-pyrrolo[3,4-d]pyrimidin-5-yl)benzonitrile (step 1)(573 mg, 0.983 mmol) was dissolved in DCM (20 ml) to form a clear brown solution and passed through 2×500 mg Isolute® Si-TMT (silica bound equivalent of 2,4,6-trimercatotriazine) cartridges to afford a colourless solution. The solution was placed under a nitrogen atmosphere and whilst stirring rapidly, treated dropwise with triethylsilane (1.571 ml, 9.83 mmol) followed TFA (3.79 ml, 49.2 mmol). After stirring at RT for 1 h, the reaction mixture was concentrated under reduced pressure to yield a white solid. The isolated crude product was triturated with diethyl ether and dried in a vacuum oven at 50° C. to afford the title compound;

後処理

  1. customto form a clear brown solution
  2. customto afford a colourless solution
  3. stirringAfter stirring at RT for 1 h
  4. concentrationthe reaction mixture was concentrated under reduced pressure
  5. customto yield a white solid
  6. customThe isolated crude product
  7. customwas triturated with diethyl ether
  8. customdried in a vacuum oven at 50° C.

出典と根拠

ORDレコード
ord-88988c59cc494c8d9684180980f01e6f
出典データセット
uspto-grants-2016_06
特許番号
US09359381B2

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