P,P-Diphenylphosphinic azide → 1-(4-Dimethylaminomethyl-2-methoxy-phenyl)-3-(5-methyl-pyrazin-2-yl)-urea

HRID 1830786Notes

Reaction equation

HRID 1830786 reaction equation
C1(P(N=[N+]=[N-])(C2C=CC=CC=2)=O)C=CC=CC=1.[CH3:18][N:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[C:24]([O:29][CH3:30])[CH:23]=1)[CH3:20].[CH3:31][C:32]1[N:33]=[CH:34][C:35]([NH:38][C:39](N)=[O:40])=[N:36][CH:37]=1>>[CH3:20][N:19]([CH2:21][C:22]1[CH:27]=[CH:26][C:25]([NH:28][C:39]([NH:38][C:35]2[CH:34]=[N:33][C:32]([CH3:31])=[CH:37][N:36]=2)=[O:40])=[C:24]([O:29][CH3:30])[CH:23]=1)[CH3:18]

Participants

4

Reactant 3

HCID 199401P,P-Diphenylphosphinic azideHCID 22046266(5-Methyl-pyrazin-2-yl)-ureaHCID 220462864-((Dimethylamino)methyl)-2-methoxyaniline

Product 1

HCID 220464981-(4-Dimethylaminomethyl-2-methoxy-phenyl)-3-(5-methyl-pyrazin-2-yl)-urea

Procedure

According to the diphenylphosphoryl azide method described above for compound 336, 4-dimethylaminomethyl-2-methoxy-phenylamine was converted to the (5-methyl-pyrazin-2-yl)-urea. The crude product was purified by preparative TLC, eluting with 5% MeOH in CH2Cl2. 1H NMR (400 MHz, d6-DMSO): δ11.21 (s, 1H), 8.95 (s, 1H), 8.39 (s, 1H), 8.21 (d, J=7.83 Hz, 1H), 8.04 (s, 1H), 7.01 (s, 1H), 6.89 (d, J=7.83 Hz, 1H), 3.98 (s, 3H), 3.92 (s, 2H), 2.26 (s, 3H), 2.24 (s, 6H). MS APCI-Pos, M+1=316.0.

Workup

  1. customThe crude product was purified by preparative TLC
  2. washeluting with 5% MeOH in CH2Cl2

Sources & evidence

ORD record
ord-57005d5dcb4e4dcaa7d8240269081724
Source dataset
uspto-grants-2006_06
Patent number
US07067506B2

Reaction notes

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