3,4,5-Trimethoxyaniline → 4-(2-chloropyridin-3-yl)-N-(3,4,5-trimethoxyphenyl)-1,3,5-triazin-2-amine

HRID 983448Notes

Reaction equation

HRID 983448 reaction equation
Cl[C:2]1[N:7]=[C:6]([C:8]2[C:9]([Cl:14])=[N:10][CH:11]=[CH:12][CH:13]=2)[N:5]=[CH:4][N:3]=1.[CH3:15][O:16][C:17]1[CH:18]=[C:19]([CH:21]=[C:22]([O:26][CH3:27])[C:23]=1[O:24][CH3:25])[NH2:20]>CCN(CC)CC>[Cl:14][C:9]1[C:8]([C:6]2[N:5]=[CH:4][N:3]=[C:2]([NH:20][C:19]3[CH:21]=[C:22]([O:26][CH3:27])[C:23]([O:24][CH3:25])=[C:17]([O:16][CH3:15])[CH:18]=3)[N:7]=2)=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 322853,4,5-TrimethoxyanilineHCID 161089782-Chloro-4-(2-chloro-pyridin-3-yl)-[1,3,5]triazine

Product 1

HCID 161090054-(2-chloropyridin-3-yl)-N-(3,4,5-trimethoxyphenyl)-1,3,5-triazin-2-amineYield 89.2%

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

2-Chloro-4-(2-chloro-pyridin-3-yl)-[1,3,5]triazine (1.7 g, 7.5 mmol) was stirred overnight at RT with 3,4,5-trimethoxyaniline (1.5 g, 8.3 mmol) in IpOH (200 mL). After addition of Et3N (2 ml), stirring was continued for an additional day. The mixture was concentrated, triturated with t-BuOMe and filtered, rinsing with a small amount of IpOH. The [4-(2-chloro-pyridin-3-yl)-[1,3,5]triazin-2-yl]-(3,4,5-trimethoxy-phenyl)amine (2.5 g) was isolated as the Et3HN+Cl− salt. Part of this material was filtered through a plug of silica and analyzed. MS m/z=374 [M+H]+; 3H). Calc'd for C17H16ClN5O3: 373.09. Remaining material was used without filtering in the next step.

Workup

  1. waitwas continued for an additional day
  2. concentrationThe mixture was concentrated
  3. customtriturated with t-BuOMe
  4. filtrationfiltered
  5. washrinsing with a small amount of IpOH

Sources & evidence

ORD record
ord-6d7c5039d42b4693ad8116c1a2c0fc87
Source dataset
uspto-grants-2005_03
Patent number
US06864255B2

Reaction notes

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