4-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehyde → HCID 89814189, compound

HRID 522733

Reaction equation

HRID 522733 reaction equation
[NH2:1][C:2]1[C:3]([F:13])=[CH:4][C:5]([Br:12])=[C:6]([CH2:8][C:9](=O)[CH3:10])[CH:7]=1.[NH2:14][C:15]1[C:20]([CH:21]=O)=[CH:19][N:18]=[C:17]([S:23][CH3:24])[N:16]=1.[O-]CC.[Na+]>CCO>[Br:12][C:5]1[C:6]([C:8]2[C:9]([CH3:10])=[N:14][C:15]3[N:16]=[C:17]([S:23][CH3:24])[N:18]=[CH:19][C:20]=3[CH:21]=2)=[CH:7][C:2]([NH2:1])=[C:3]([F:13])[CH:4]=1

Participants

5

Reactant 3

HCID 2957694-Amino-2-(methylsulfanyl)pyrimidine-5-carbaldehydeHCID 2723922Sodium ethoxideHCID 898138911-(5-Amino-2-bromo-4-fluorophenyl)propan-2-one

Product 1

HCID 89814189HCID 89814189, compoundYield 16.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Treat a solution of 1-(5-amino-2-bromo-4-fluorophenyl)propan-2-one (5 g, 27.62 mmol) and 4-amino-2-methylsulfanyl-pyrimidine-5-carbaldehyde (4.67 g, 27.62 mmol) in EtOH (30 mL) with sodium ethoxide (3.76 g, 55.25 mmol) and stir at RT for 12 h. Concentrate the mixture to dryness, treat with water, extract with EtOAc (3×), wash the combined organics with brine, dry with Na2SO4, concentrate and purify by silica gel chromatography (EtOAc/Pet Ether, 1:4) to afford the title compound (1.7 g, 16% yield). MS (m/z): 379.1/381.1 (M+1).

Workup

  1. concentrationConcentrate the mixture to dryness
  2. additiontreat with water
  3. extractionextract with EtOAc (3×)
  4. washwash the combined organics with brine
  5. dry with materialdry with Na2SO4
  6. concentrationconcentrate
  7. custompurify by silica gel chromatography (EtOAc/Pet Ether, 1:4)

Sources & evidence

ORD record
ord-a4a069c1044e4d92b8eea34500bf7c52
Source dataset
uspto-grants-2016_05
Patent number
US09334267B2

Linked notes

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