Acridan → n-[(2,4-Diaminopyrimidin-6-yl)methyl]-9,10-dihydroacridine

HRID 1827707Notes

Reaction equation

HRID 1827707 reaction equation
[NH2:1][C:2]1[N:11]=[C:10](N)[C:9]2[C:4](=[N:5]C=C(CN(C3C=CC=CC=3)C3C=CC=CC=3)N=2)[N:3]=1.[CH:27]1[C:40]2[CH2:39][C:38]3[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=3)[NH:32][C:31]=2[CH:30]=[CH:29][CH:28]=1.[H-].[Na+].Br.N[C:45]1N=C(N)C(CBr)=CN=1>>[NH2:1][C:2]1[N:3]=[C:4]([NH2:5])[CH:9]=[C:10]([CH2:45][N:32]2[C:33]3[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=3)[CH2:39][C:40]3[CH:27]=[CH:28][CH:29]=[CH:30][C:31]2=3)[N:11]=1

Participants

5

Reactant 4

HCID 7106AcridanHCID 24758Sodium hydrideHCID 4862426-[(N-phenylanilino)methyl]pteridine-2,4-diamineHCID 220629815-(Bromomethyl)pyrimidine-2,4-diamine hydrobromide

Product 1

HCID 22062985n-[(2,4-Diaminopyrimidin-6-yl)methyl]-9,10-dihydroacridine

Procedure

N-[(2,4-Diaminopyrimidin-6-yl)methyl]-9,10-dihydroacridine (Formula I: Ar=2,4-diaminopyrimidin-5-yl; W=CH2; X=N; Z=CH2; m=n=0) is prepared similarly to N-[(2,4-diaminopteridin-6-yl)methyl]-N,N-diphenylamine as disclosed above by using 9,10-dihydroacridine (134 mg, 0.8 mmol), NaH (50 mg, 2.1 mmol), and 2,4-diamino-5-bromomethylpyrimidine hydrobromide (86 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-681a074b3b88443c9b55d49cbb3f1be5
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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