Water → HCID 178483034, compound

HRID 2422173Notes

Reaction equation

HRID 2422173 reaction equation
[Cl:1][C:2]1[C:7]([CH2:8][C:9]#[N:10])=[C:6]([N:11]([CH3:13])[CH3:12])[N:5]=[C:4]([CH2:14][C:15]2[CH:20]=[CH:19][C:18](NC(C3C=CC4C(=CC=CC=4)C=3)=O)=[CH:17][CH:16]=2)[N:3]=1.[N-:34]=[N+:35]=[N-:36].[Na+].[CH3:38][CH:39](O)[CH3:40].[OH2:42]>[Br-].[Br-].[Zn+2].CCOC(C)=O.O1CCOCC1>[Cl:1][C:2]1[C:7]([CH2:8][C:9]2[NH:10][N:36]=[N:35][N:34]=2)=[C:6]([N:11]([CH3:13])[CH3:12])[N:5]=[C:4]([CH2:14][C:15]2[CH:16]=[CH:17][CH:18]=[CH:19][C:20]=2[C:39]2[C:40]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH:15]=[C:14]([C:4]([NH2:3])=[O:42])[CH:38]=2)[N:3]=1

Participants

8

Reactant 4

HCID 962Water2×HCID 3776IsopropanolHCID 33557Sodium AzideHCID 46908652HCID 46908652, compound

Product 1

HCID 178483034HCID 178483034, compoundYield 31%

Reagents, catalysts & solvents 3

HCID 10421208Zinc bromideCatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

A solution containing N-(4-{[4-chloro-5-(cyanomethyl)-6-(dimethylamino)pyrimidin-2-yl]methyl}phenyl)-2-naphthamide (0.279 g, 0.61 mmol), sodium azide (0.159 g, 2.44 mmol), zinc dibromide (0.345 g, 1.55 mmol), 2-propanol (2.7 mL), water (4 mL), and 1,4-dioxane (5 mL) was heated at reflux for 24 hours. After cooling to room temperature, EtOAc (4 mL) was added and stirring was continued for 2 hours. The resulting mixture was poured into water and the precipitate thus formed was collected by suction, rinsed with water and MeOH, and dried in vacuo to give N-(4-{([4-chloro-6-(dimethylamino)-5-(1H-tetrazol-5-ylmethyl)pyrimidin-2-yl]methyl}-phenyl)-2-naphthamide as a light beige solid (0.095 g, 31%).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 24 hours
  3. customthe precipitate thus formed
  4. customwas collected by suction
  5. washrinsed with water and MeOH
  6. customdried in vacuo

Sources & evidence

ORD record
ord-8e228d0a3abb43f48a1a1aa6e1eed75b
Source dataset
uspto-grants-2011_06
Patent number
US07960393B2

Reaction notes

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