Diisopropylethylamine → 4,6-Dimethoxy-2-(alpha-fluorobenzyl) pyrimidine

HRID 1440962Notes

Reaction equation

HRID 1440962 reaction equation
Cl.Cl.[C:3](=[NH:11])([O:9][CH3:10])[CH2:4][C:5](=[NH:8])[O:6][CH3:7].C(N(C(C)C)C(C)C)C.[F:21][CH:22]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:23](Cl)=O>ClCCl>[CH3:7][O:6][C:5]1[CH:4]=[C:3]([O:9][CH3:10])[N:11]=[C:23]([CH:22]([F:21])[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[N:8]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 12896693Dimethyl malonimidate dihydrochlorideHCID 149495282-Fluoro-2-phenylacetyl chloride

Product 1

HCID 541012184,6-Dimethoxy-2-(alpha-fluorobenzyl) pyrimidineYield 103.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

Dimethyl malonimidate dihydrochloride (11.0 g) was suspended in dichloromethane (100 ml) at -40° C. Ethyl diisopropylamine (38.9 ml) was added dropwise over 15 minutes at -40° C., followed by 2-fluoro-2-phenylacetyl chloride (11.0 g) in dichloromethane (15 ml) over 10 minutes at -40° C. The reaction mixture was allowed to warm to room temperature and stand overnight. It was then diluted further with dichloromethane, washed with ammonium chloride solution, then with water, and was dried over magnesium sulfate. The dichloromethane solution was evaporated to dryness to give 13.9 g of the desired product.

Workup

  1. washwashed with ammonium chloride solution
  2. dry with materialwith water, and was dried over magnesium sulfate
  3. customThe dichloromethane solution was evaporated to dryness

Sources & evidence

ORD record
ord-6138cea4710c432493891253a750fc80
Source dataset
uspto-grants-1996_03
Patent number
US05502028

Reaction notes

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