Carbazole → n-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]carbazole

Reaktionsgleichung

[NH2:1][C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[C:10]([CH2:11][N:12]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[CH:9][S:8][C:6]=2[N:7]=1.NC1N=C(N)C2C(C)=CSC=2N=1.C1C2NC3C(=CC=CC=3)C=2C=CC=1>>[NH2:1][C:2]1[N:3]=[C:4]([NH2:25])[C:5]2[C:10]([CH2:11][N:12]3[C:19]4[CH:20]=[CH:21][CH:22]=[CH:23][C:24]=4[C:18]4[C:13]3=[CH:14][CH:15]=[CH:16][CH:17]=4)=[CH:9][S:8][C:6]=2[N:7]=1

Komponenten

Edukt 3

HCID 6854Carbazole

HCID 9906281n-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-n,n-diphenylamine

HCID 12659534Thieno[2,3-d]pyrimidine-2,4-diamine, 5-methyl-

Produkt 1

HCID 9928153n-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]carbazole

Versuchsvorschrift

N-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]carbazole (Formula I: Ar=2,4-diaminothieno[2,3-d]pyrimidin-5-yl; W=CH2; X=N; Z=chemical bond; m=n=0) is prepared similarly to N-[(2,4-diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-N,N-diphenylamine as disclosed in Example 11 above by using 2,4-diamino-5-methylthieno[2,3-d]pyrimidine (1.3 g, 7.2 mmol) in Step 1 and carbazole (129 mg, 0.8 mmol) in Step 3. The final product and its intermediates can be purified by chromatography.