Acridan → n-[(2,4-Diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]-9,10-dihydroacridine

HRID 1827703Notes

Reaction equation

HRID 1827703 reaction equation
NC1N=C(N)C2C(=NC=C(CN(C3C=CC=CC=3)C3C=CC=CC=3)N=2)N=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.[NH2:44][C:45]1[N:46]=[C:47]([NH2:57])[C:48]2[CH:54]=[C:53]([CH2:55]Br)[CH:52]=[N:51][C:49]=2[N:50]=1>>[NH2:44][C:45]1[N:46]=[C:47]([NH2:57])[C:48]2[CH:54]=[C:53]([CH2:55][N:32]3[C:33]4[C:38](=[CH:37][CH:36]=[CH:35][CH:34]=4)[CH2:39][C:40]4[CH:27]=[CH:28][CH:29]=[CH:30][C:31]3=4)[CH:52]=[N:51][C:49]=2[N:50]=1

Participants

5

Reactant 4

HCID 7106AcridanHCID 24758Sodium hydrideHCID 4862426-[(N-phenylanilino)methyl]pteridine-2,4-diamineHCID 220630092,4-Diamino-6-bromomethylpyrido[2,3-d]pyrimidine hydrobromide

Product 1

HCID 22063020n-[(2,4-Diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]-9,10-dihydroacridine

Procedure

N-[(2,4-Diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]-9,10-dihydroacridine (Formula I: Ar=2,4-diaminopyrido[2,3-d]pyrimidin-6-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-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-9e54cd1bd23a461e8039b67d4ac9c878
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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