Hydrochloric Acid → 4-(3-Methoxyanilino)-2,6-di(2-pyridinyl)pyrimidine

HRID 2084155Notes

Reaction equation

HRID 2084155 reaction equation
Cl[C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:3]=1.[CH3:20][O:21][C:22]1[CH:27]=[CH:26][CH:25]=[C:24]([NH2:28])[CH:23]=1.Cl.[OH-].[Na+]>O.C(O)C>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:25]=[CH:26][CH:27]=1)[NH:28][C:2]1[CH:7]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][N:15]=2)[N:3]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 108243-MethoxyanilineHCID 14798Sodium HydroxideHCID 27670664-Chloro-2,6-di(2-pyridinyl)pyrimidine

Product 1

HCID 227325004-(3-Methoxyanilino)-2,6-di(2-pyridinyl)pyrimidineYield 60.5%

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

A mixture 4-chloro-2,6-di(2-pyridinyl)pyrimidine (25 mg, 0.093 mmol), m-anisidine (16 μl, 0.140 mmol) and 2N HCl (75 μl) in water:ethanol (2:1, 10 ml) was refluxed for 24 h. The mixture was cooled to room temperature and basified with aqueous 2N NaOH to pH 10-12. The resulting precipitate was filtered, washed with water and aqueous ethanol to give a yellow solid (20 mg, 60%). 1H NMR (CDCl3): 8.87-8.85 (m, 1H), 8.69-8.61 (m, 3H), 7.95 (s, 1H), 7.92-7.84 (m, 2H), 7.44-7.36 (m, 2H), 7.33 (d, J=8.1 Hz, 1H), 7.30 (s, 1H), 7.05 (t, J=2.1 Hz, 1H), 6.98 (dd, J=2.1, 8.1 Hz, 1H), 6.79-6.75 (m, 1H), 3.86 (s, 3H).

Workup

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with water and aqueous ethanol

Sources & evidence

ORD record
ord-1bcb95bd9393417fb4bdfd4d28ea1a12
Source dataset
uspto-grants-2004_04
Patent number
US06716851B2

Reaction notes

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