Sodium Hydroxide → 7-(1-bromoethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-one

HRID 1429782Notes

Reaction equation

HRID 1429782 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([NH2:7])[S:5][CH:6]=1.[Br:8][CH:9]([CH3:17])[C:10](=O)[CH2:11][C:12](OC)=[O:13].[OH-].[Na+]>C(Cl)Cl>[Br:8][CH:9]([C:10]1[N:7]=[C:4]2[S:5][CH:6]=[C:2]([CH3:1])[N:3]2[C:12](=[O:13])[CH:11]=1)[CH3:17]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 741432-Amino-4-methylthiazoleHCID 9815681Methyl 4-bromo-3-oxopentanoate

Product 1

HCID 581114377-(1-bromoethyl)-3-methyl-5H-[1,3]thiazolo[3,2-a]pyrimidin-5-oneYield 42.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
110 °C

Procedure

To a manually stirred polyphosphoric acid (80 g, 800 mmol) in a 1000 mL beaker was added 4-methyl-1,3-thiazol-2-amine (Aldrich, 16 g, 140 mmol), followed by methyl 4-bromo-3-oxopentanoate (34.9 g, 167 mmol). The mixture was heated with stirring at 110° C. for 5 h. After cooling, the dark slurry was transferred into 300 g of ice. The pH of the mixture was adjust to 6-7 with 10% sodium hydroxide. The aqueous layer was discarded and the dark oil layer was diluted with methylene chloride and washed with 1N NaOH, brine, dried over magnesium sulfate, and evaporated to dryness to yield the desired product (16.2 g, 42.6%). LCMS calculated for C9H10BrN2OS (M+H)+: m/z=273.0. Found: 273.1.

Workup

  1. temperatureThe mixture was heated
  2. temperatureAfter cooling
  3. washwashed with 1N NaOH, brine
  4. dry with materialdried over magnesium sulfate
  5. customevaporated to dryness

Sources & evidence

ORD record
ord-289ddbe771e44274b7f88c9ae0beb671
Source dataset
uspto-grants-2015_01
Patent number
US08940752B2

Reaction notes

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