Carbazole → 6-(Carbazol-9-ylmethyl)pteridine-2,4-diamine

HRID 1827696Notes

Reaction equation

HRID 1827696 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:8]=2)[N:3]=1.C1C2NC3C(=CC=CC=3)C=2C=CC=1.[H-].[Na+].Br.NC1N=C(N)C2C(=NC=C(CBr)N=2)N=1>>[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]3[C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=4[C:26]4[C:21]3=[CH:22][CH:23]=[CH:24][CH:25]=4)[N:8]=2)[N:3]=1

Participants

5

Reactant 4

HCID 6854CarbazoleHCID 24758Sodium hydrideHCID 4862426-[(N-phenylanilino)methyl]pteridine-2,4-diamineHCID 125032426-(Bromomethyl)-2-imino-2,3-dihydropteridin-4-amine--hydrogen bromide (1/1)

Product 1

HCID 4862446-(Carbazol-9-ylmethyl)pteridine-2,4-diamine

Procedure

N-[(2,4-Diaminopteridin-6-yl)methyl]carbazole (Formula I: Ar=2,4-diaminopteridin-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-bromomethylpteridine 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-c3d2195b28bf4f29abda97cc8e9a8097
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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