3-Amino-1-propanol → HCID 57845437, compound

HRID 2424983Notes

Reaction equation

HRID 2424983 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[NH2:10][CH2:11][CH2:12][CH2:13][OH:14].C(=O)([O-])[O-].[Na+].[Na+]>C(O)C>[Cl:1][C:2]1[N:7]=[C:6]([NH:10][CH2:11][CH2:12][CH2:13][OH:14])[C:5]([F:9])=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 90863-Amino-1-propanolHCID 10340Sodium CarbonateHCID 2507052,4-Dichloro-5-fluoropyrimidine

Product 1

HCID 57845437HCID 57845437, compoundYield 51.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2,4-dichloro-5-fluoropyrimidine (15.0 g, 89.8 mmol) in ethanol (300 mL) were added 3-amino-1-propanol (8.23 mL, 107.8 mmol) and sodium carbonate (47.6 g, 449 mmol). The reaction mixture was vigorously stirred at rt for 72 h. Then the mixture was filtered through Celite®. The filtrate was concentrated under reduced pressure, and the residue was purified by silica gel flash chromatography (100% EtOAc) to give the title compound as a white solid (9.5 g, 51%). LC/MS m/z 206.3 (M+H)+; 1H NMR (300 MHz, CD2Cl2) δ 1.85 (quintet, 2H), 3.55 (t, 2H), 3.65 (t, 2H), 4.85-4.98 (br, 2H), 7.85 (d, 1H).

Workup

  1. filtrationThen the mixture was filtered through Celite®
  2. concentrationThe filtrate was concentrated under reduced pressure
  3. customthe residue was purified by silica gel flash chromatography (100% EtOAc)

Sources & evidence

ORD record
ord-eea8db1cd2d3485ab89fbb9acefbb4d8
Source dataset
uspto-grants-2011_06
Patent number
US07964622B2

Reaction notes

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