Chloroacetaldehyde → 2-fluoro-4-imidazo[1,2-a]pyrimidin-6-yl-N-methylbenzamide

HRID 500127Notes

Reaction equation

HRID 500127 reaction equation
[NH2:1][C:2]1[N:7]=[CH:6][C:5]([C:8]2[CH:17]=[CH:16][C:11]([C:12]([NH:14][CH3:15])=[O:13])=[C:10]([F:18])[CH:9]=2)=[CH:4][N:3]=1.Cl[CH2:20][CH:21]=O>C(O)(C)C>[F:18][C:10]1[CH:9]=[C:8]([C:5]2[CH:4]=[N:3][C:2]3[N:7]([CH:20]=[CH:21][N:1]=3)[CH:6]=2)[CH:17]=[CH:16][C:11]=1[C:12]([NH:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 33ChloroacetaldehydeHCID 672245484-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzamide

Product 1

HCID 672248512-fluoro-4-imidazo[1,2-a]pyrimidin-6-yl-N-methylbenzamideYield 88.8%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 4-(2-aminopyrimidin-5-yl)-2-fluoro-N-methylbenzamide (123 mg, 0.5 mmol) and chloroacetaldehyde (0.318 mL, 2.5 mmol) in isopropyl alcohol (4 mL) was stirred at 90° C. for 4 h. The solvent was removed under vacuum and the residue was triturated with ethyl acetate and hexanes. The solid formed was collected and dried under reduced pressure to give the desired product (120 mg, 88.8%). LCMS: (M+H)=271.0.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe residue was triturated with ethyl acetate and hexanes
  3. customThe solid formed
  4. customwas collected
  5. customdried under reduced pressure

Sources & evidence

ORD record
ord-b4befdcaa61a4a2a8f5d493dfd20df7c
Source dataset
uspto-grants-2010_08
Patent number
US07767675B2

Reaction notes

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