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

HRID 1827699Notes

Reaction equation

HRID 1827699 reaction equation
[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

Participants

4

Reactant 3

HCID 6854CarbazoleHCID 9906281n-[(2,4-Diaminothieno[2,3-d]pyrimidin-5-yl)methyl]-n,n-diphenylamineHCID 12659534Thieno[2,3-d]pyrimidine-2,4-diamine, 5-methyl-

Product 1

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

Procedure

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.

Workup

  1. customThe final product and its intermediates can be purified by chromatography

Sources & evidence

ORD record
ord-6cdbd62d9d1245d5832f920bcacef223
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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