Dibenz(b,f)azepine → 9-[(2,4-Diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]dibenz[b,f]azepine

HRID 1827722Notes

Reaction equation

HRID 1827722 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:37]2[CH:36]=[CH:35][C:34]3[CH:38]=[CH:39][CH:40]=[CH:41][C:33]=3[NH:32][C:31]=2[CH:30]=[CH:29][CH:28]=1.[H-].[Na+].Br.[NH2:45][C:46]1[N:47]=[C:48]([NH2:58])[C:49]2[CH:55]=[C:54]([CH2:56]Br)[CH:53]=[N:52][C:50]=2[N:51]=1>>[NH2:45][C:46]1[N:47]=[C:48]([NH2:58])[C:49]2[CH:55]=[C:54]([CH2:56][C:38]3[C:34]4[CH:35]=[CH:36][C:37]5[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=5[NH:32][C:33]=4[CH:41]=[CH:40][CH:39]=3)[CH:53]=[N:52][C:50]=2[N:51]=1

Participants

5

Reactant 4

HCID 9212Dibenz(b,f)azepineHCID 24758Sodium hydrideHCID 4862426-[(N-phenylanilino)methyl]pteridine-2,4-diamineHCID 220630092,4-Diamino-6-bromomethylpyrido[2,3-d]pyrimidine hydrobromide

Product 1

HCID 220630329-[(2,4-Diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]dibenz[b,f]azepine

Procedure

9-[(2,4-Diaminopyrido[2,3-d]pyrimidin-6-yl)methyl]dibenz[b,f]azepine (Formula I: Ar=2,4-diaminopyrido[2,3-d]pyrimidin-6-yl; W=CH2; X=N; Z=CH═CH; m=n=0) is prepared similarly to N-[(2,4-diaminopteridin-6-yl)methyl]-N,N-diphenylamine as disclosed above by using dibenz[b,f]azepine (154 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-24d32209245e4f8189faedb739824467
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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