2,4-Dichloropyrimidine → HCID 86617115, compound

HRID 1723713Notes

Reaction equation

HRID 1723713 reaction equation
[N:1]1[O:2][CH:3]=[C:4]2[C:9]=1[CH2:8][CH2:7][NH:6][CH2:5]2.Cl[C:11]1[N:16]=[C:15]([Cl:17])[CH:14]=[CH:13][N:12]=1.CCN(C(C)C)C(C)C>CCO>[Cl:17][C:15]1[N:16]=[CH:11][N:12]=[C:13]([N:6]2[CH2:7][CH2:8][C:9]3=[N:1][O:2][CH:3]=[C:4]3[CH2:5]2)[CH:14]=1

Participants

5

Reactant 3

HCID 775312,4-DichloropyrimidineHCID 81531DiisopropylethylamineHCID 469119714,5,6,7-Tetrahydro[1,2]oxazolo[4,3-c]pyridine

Product 1

HCID 86617115HCID 86617115, compoundYield 69.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
150 °C

Procedure

4,5,6,7-Tetrahydro-isoxazolo[4,3-c]pyridine (162.0 mg, 1.3 mmol), 2,4-dichloropyrimidine (213.9 mg, 1.4 mmol), and DIPEA (421.6 mg, 0.57 mL, 3.3 mmol) in 3 mL of EtOH were added to a 5 mL microwave vial and microwave heated for 5 minutes at 150° C. The solvent was evaporated and the residue purified by chromatography (Biotage 25 S eluting with 100 mL each of 0, 10, 20, 30, and 40% THF/petroleum ether) to afford 215.3 mg, (69.7% yield) of the product. MS 237.2 (AP+, 100).

Workup

  1. customThe solvent was evaporated
  2. customthe residue purified by chromatography (Biotage 25 S eluting with 100 mL each of 0, 10, 20, 30, and 40% THF/petroleum ether)

Sources & evidence

ORD record
ord-46a5d4fc11db402d85910aaa2a733efa
Source dataset
uspto-grants-2009_02
Patent number
US07485641B2

Reaction notes

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