Carbazole → n-[(2,4-Diaminopyrido[2,3-d]pyrimdin-6-yl)methyl]carbazole

HRID 1827697Notes

Reaction equation

HRID 1827697 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=[N:5][CH:6]=[C:7]([CH2:13][N:14]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)N=2)[N:3]=1.[CH:27]1C2NC3C(=CC=CC=3)C=2C=CC=1.[H-].[Na+].Br.NC1N=C(N)C2C=C(CBr)C=NC=2N=1>>[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[CH:27]=[C:7]([CH2:13][N:14]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:20]4[C:15]3=[CH:16][CH:17]=[CH:18][CH:19]=4)[CH:6]=[N:5][C:4]=2[N:3]=1

Participants

5

Reactant 4

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 4862426-[(N-phenylanilino)methyl]pteridine-2,4-diamineHCID 220630092,4-Diamino-6-bromomethylpyrido[2,3-d]pyrimidine hydrobromide

Product 1

HCID 9884356n-[(2,4-Diaminopyrido[2,3-d]pyrimdin-6-yl)methyl]carbazole

Procedure

N-[(2,4-Diaminopyrido[2,3-d]pyrimdin-6-yl)methyl]carbazole (Formula I: Ar=2,4-diaminopyrido[2,3-[pyrindin-6-yl; W=CH2; X=N; Z=chemical bond; m=n=0) is prepared similarly to N-[(2,4-diaminopteridin-6-yl)methyl]N,N-diphenylamine as disclosed above by using carbazole (129 mg, 0.77 mmol), NaH (50 mg, 2.1 mmol), and 2,4-diamino-6-bromomethylpyrido[2,3-d]pyrimidine hydrobromide (100 mg, 0.3 mmol). The product can be purified by chromatography.

Workup

  1. customThe product can be purified by chromatography

Sources & evidence

ORD record
ord-316d29af867a4e97bda5f475272e3e51
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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