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

HRID 1765209Notes

Reaction equation

HRID 1765209 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-877ac5200cd44d48bc3b34934dbe3328
Source dataset
uspto-grants-2007_06
Patent number
US07226927B2

Reaction notes

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