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

HRID 1827698Notes

Reaction equation

HRID 1827698 reaction equation
[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[C:4](=N[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:8]=2)[N:3]=1.[CH:27]1C2NC3C(=CC=CC=3)C=2C=CC=1.[H-].[Na+].Br.NC1N=C(N)C2N=C(CBr)C=CC=2N=1>>[NH2:1][C:2]1[N:11]=[C:10]([NH2:12])[C:9]2[N:8]=[C:7]([CH2:13][N:14]3[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:26]=4[C:16]4[C:15]3=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH:6]=[CH:27][C:4]=2[N:3]=1

Participants

5

Reactant 4

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 4862426-[(N-phenylanilino)methyl]pteridine-2,4-diamineHCID 220629822,4-Diamino-6-bromomethylpyrido[3,2-d]pyrimidine hydrobromide

Product 1

HCID 9862774n-[(2,4-Diaminopyrido[3,2-d]pyrimidin-6-yl)methyl]carbazole

Procedure

N-[(2,4-Diaminopyrido[3,2-d]pyrimidin-6-yl)methyl]carbazole (Formula I: Ar=2,4-diaminopyrido[2,3-d]pyrimidin-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[3,2-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-121d42bbce42469fa0695ddb32a8e832
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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