Sodium hydride → 9-[(2,4-Diaminopyrimidin-5-yl)methyl]-9,10-dihydrodibenz[b,f]azepine

HRID 1827720Notes

Reaction equation

HRID 1827720 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[C:31](=[N:32][C:33]3[CH:41]=[CH:40][CH2:39][CH2:38][C:34]=3[CH2:35][CH:36]=2)[CH:30]=[CH:29][CH:28]=1.[H-].[Na+].Br.[NH2:45][C:46]1[N:51]=[C:50]([NH2:52])[C:49]([CH2:53]Br)=[CH:48][N:47]=1>>[NH2:45][C:46]1[N:51]=[C:50]([NH2:52])[C:49]([CH2:53][CH:38]2[C:34]3[CH2:35][CH:36]=[C:37]4[CH:27]=[CH:28][CH:29]=[CH:30][C:31]4=[N:32][C:33]=3[CH:41]=[CH:40][CH2:39]2)=[CH:48][N:47]=1

Participants

5

Reactant 4

HCID 24758Sodium hydrideHCID 4862426-[(N-phenylanilino)methyl]pteridine-2,4-diamineHCID 220629815-(Bromomethyl)pyrimidine-2,4-diamine hydrobromideHCID 695914299,10-Dihydrodibenz[b,f]azepine

Product 1

HCID 695911339-[(2,4-Diaminopyrimidin-5-yl)methyl]-9,10-dihydrodibenz[b,f]azepine

Procedure

9-[(2,4-Diaminopyrimidin-5-yl)methyl]-9,10-dihydrodibenz[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 9,10-dihydrodibenz[b,f]azepine (158 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-9e038303e79e4d039732e6b77794cbef
Source dataset
uspto-grants-2006_06
Patent number
US07056911B1

Reaction notes

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