2-Amino-4-methylpyrimidine → 4-[(1E)-2-(5-Bromo-3-pyridinyl)ethenyl]-2-pyrimidinamine

HRID 2307787Notes

Reaction equation

HRID 2307787 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:8]=O)[CH:5]=[N:6][CH:7]=1.[NH2:10][C:11]1[N:16]=[C:15]([CH3:17])[CH:14]=[CH:13][N:12]=1>C(O)=O.O.[OH-].[Na+]>[Br:1][C:2]1[CH:3]=[C:4](/[CH:8]=[CH:17]/[C:15]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:10])[N:16]=2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 2

HCID 79392-Amino-4-methylpyrimidineHCID 27847345-Bromo-3-pyridinecarboxaldehyde

Product 1

HCID 699177774-[(1E)-2-(5-Bromo-3-pyridinyl)ethenyl]-2-pyrimidinamineYield 71.4%

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 14798Sodium HydroxideSolvent

Procedure

A solution of 5-bromo-pyridine-3-carbaldehyde (436 mg, 2.34 mmol) and 2-amino-4-methylpyrimidine (246 mg, 2.35 mmol) in formic acid (96%, 3 mL) was heated for 18 h. After cooling to rt, it was then diluted with water and basified to pH ˜13 with 1 N NaOH. The mixture was then extracted with methylene chloride. The combined extracts was washed with water (1×), dried over MgSO4 and concentrated. The residue was chromatographed on silica gel eluting with CH2Cl2:MeOH:NH4OH (100:5:0.5) to give the title compound (463 mg, 71%). MS (DCI/NH3) m/z 277, 279 (M+1)+.

Workup

  1. extractionThe mixture was then extracted with methylene chloride
  2. washThe combined extracts was washed with water (1×)
  3. dry with materialdried over MgSO4
  4. concentrationconcentrated
  5. customThe residue was chromatographed on silica gel eluting with CH2Cl2:MeOH:NH4OH (100:5:0.5)

Sources & evidence

ORD record
ord-6d7ce6526438404abee9095356389cf0
Source dataset
uspto-grants-2004_12
Patent number
US06831175B2

Reaction notes

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