1,8-Diazabicyclo(5.4.0)undec-7-ene → 4-(5-(1-azidoethyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine

HRID 1621929Notes

Reaction equation

HRID 1621929 reaction equation
[CH3:1][O:2][C:3]1[CH:45]=[CH:44][C:6]([CH2:7][N:8]([CH2:35][C:36]2[CH:41]=[CH:40][C:39]([O:42][CH3:43])=[CH:38][CH:37]=2)[C:9]2[N:14]=[C:13]([CH3:15])[N:12]=[C:11]([C:16]3[CH:17]=[C:18]([CH:32](O)[CH3:33])[CH:19]=[N:20][C:21]=3[NH:22][C:23]3[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[CH:28]=3)[N:10]=2)=[CH:5][CH:4]=1.P([N:62]=[N+:63]=[N-:64])(OC1C=CC=CC=1)(OC1C=CC=CC=1)=O.N12CCCN=C1CCCCC2>C1(C)C=CC=CC=1.CCOC(C)=O>[N:62]([CH:32]([C:18]1[CH:17]=[C:16]([C:11]2[N:12]=[C:13]([CH3:15])[N:14]=[C:9]([N:8]([CH2:7][C:6]3[CH:44]=[CH:45][C:3]([O:2][CH3:1])=[CH:4][CH:5]=3)[CH2:35][C:36]3[CH:37]=[CH:38][C:39]([O:42][CH3:43])=[CH:40][CH:41]=3)[N:10]=2)[C:21]([NH:22][C:23]2[CH:24]=[N:25][C:26]([O:30][CH3:31])=[C:27]([F:29])[CH:28]=2)=[N:20][CH:19]=1)[CH3:33])=[N+:63]=[N-:64]

Participants

6

Reactant 3

HCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 123414Diphenylphosphoryl azideHCID 666112271-(5-(4-(Bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol

Product 1

HCID 866470754-(5-(1-azidoethyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amineYield 105.7%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A glass microwave reaction vessel was charged with 1-(5-(4-(bis(4-methoxybenzyl)amino)-6-methyl-1,3,5-triazin-2-yl)-6-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)ethanol (0.9 g, 1.635 mmol) in toluene (15 mL). The tube was sealed under inert atmosphere. To this suspension, diphenyl azidophosphate (0.9 mL, 4.2 mmol) and 1,8-diazabicyclo[5.4.0]undec-7-ene (0.64 mL, 4.3 mmol) were mixed, the solution was stirred for 16 h. The mixture was diluted with EtOAc, washed by saturated NH4Cl and brine, concentrated under a vacuum to provide 4-(5-(1-azidoethyl)-2-(5-fluoro-6-methoxypyridin-3-ylamino)pyridin-3-yl)-N,N-bis(4-methoxybenzyl)-6-methyl-1,3,5-triazin-2-amine (1.1 g, 92% purity, 100% yield) as a yellow solid, which was used in next step without further purification. MS (ESI positive ion) m/z: 637 (M+1).

Workup

  1. customA glass microwave reaction vessel
  2. customThe tube was sealed under inert atmosphere
  3. washwashed by saturated NH4Cl and brine
  4. concentrationconcentrated under a vacuum

Sources & evidence

ORD record
ord-36d36c7df0a84c7582da251707ce46f4
Source dataset
uspto-grants-2014_07
Patent number
US08772480B2

Reaction notes

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