Dibenz(b,f)azepine → 9-[(2,4-Diaminopyrimidin-6-yl)methyl]dibenz[b,f]azepine

HRID 1827726Notes

Reaction equation

HRID 1827726 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: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.N[C:46]1N=C(N)C(CBr)=CN=1>>[NH2:1][C:2]1[N:3]=[C:4]([NH2:5])[CH:9]=[C:10]([CH2:46][C:38]2[C:34]3[CH:35]=[CH:36][C:37]4[CH:27]=[CH:28][CH:29]=[CH:30][C:31]=4[NH:32][C:33]=3[CH:41]=[CH:40][CH:39]=2)[N:11]=1

Participants

5

Reactant 4

HCID 9212Dibenz(b,f)azepineHCID 24758Sodium hydrideHCID 4862426-[(N-phenylanilino)methyl]pteridine-2,4-diamineHCID 220629815-(Bromomethyl)pyrimidine-2,4-diamine hydrobromide

Product 1

HCID 220629769-[(2,4-Diaminopyrimidin-6-yl)methyl]dibenz[b,f]azepine

Procedure

9-[(2,4-Diaminopyrimidin-6-yl)methyl]dibenz[b,f]azepine (Formula I: Ar=2,4-diaminopyrimidin-5-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-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-b45c3c1551da432a9072790898632bce
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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