1,3-Propanediamine → 1-(3-Bromo-4-fluorophenyl)-1-(2-tetrahydropyrimidinyl)methanol

HRID 272659Notes

Reaction equation

HRID 272659 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[C:5]([CH:10]([OH:16])[C:11](=[NH:15])OCC)[CH:6]=[CH:7][C:8]=1[F:9].[NH2:17][CH2:18][CH2:19][CH2:20]N>C(O)C>[Br:2][C:3]1[CH:4]=[C:5]([CH:10]([CH:11]2[NH:15][CH2:20][CH:19]=[CH:18][NH:17]2)[OH:16])[CH:6]=[CH:7][C:8]=1[F:9]

Participants

4

Reactant 2

HCID 4281,3-PropanediamineHCID 68899226Ethyl 2-(3-Bromo-4-fluorophenyl)-2-hydroxyethanimidoate Hydrochloride

Product 1

HCID 688999571-(3-Bromo-4-fluorophenyl)-1-(2-tetrahydropyrimidinyl)methanolYield 64.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of ethyl 2-(3-bromo-4-fluorophenyl)-2-hydroxyethanimidoate Hydrochloride (39.8 g, 127 mmol) and 1,3-diaminopropane (9.43 g, 127 mmol) in ethanol is heated at 120° C. in a sealed tube overnight, cooled to room temperature, concentrated to remove the solvent, diluted with water, stirred vigorously for 1 h and filtered. The filtrate is cooled with an ice bath, made strongly basic with 1 N NaOH, cooled for 1 h in an ice bath and filtered. The filtercake is dried to afford th title compound as a white solid 23.4 g (64% yield), identified by NMR and mass spectral analyses. 1H NMR (500 MHz, CDCl3) δ 7.59 (m, 1H), 7.30 (m, 1H), 7.10 (t, J=8.4 Hz, 1H), 4.79 (s, 1H), 3.35 (m, 4H), 1.76 (m, 2H); ESI MS m/z 287 [C11H12BrFN2O+H]+.

Workup

  1. temperaturecooled to room temperature
  2. concentrationconcentrated
  3. customto remove the solvent
  4. additiondiluted with water
  5. filtrationfiltered
  6. temperatureThe filtrate is cooled with an ice bath
  7. temperaturecooled for 1 h in an ice bath
  8. filtrationfiltered
  9. customThe filtercake is dried

Sources & evidence

ORD record
ord-09ae8caf9bbe4a59b6c713aaacc671bb
Source dataset
uspto-grants-2008_11
Patent number
US07456186B2

Reaction notes

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