Triethylamine → 5-Methyl-4-((3-phenyl-isoxazol-5-yl)-methoxy-)-thieno[2,3-d]pyrimidine

HRID 57779Notes

Reaction equation

HRID 57779 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[OH:11][CH2:12][C:13]1[O:17][N:16]=[C:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:14]=1.[CH2:24](N(CC)CC)C>C(O)(C)C>[CH3:24][C:10]1[C:3]2[C:2]([O:11][CH2:12][C:13]3[O:17][N:16]=[C:15]([C:18]4[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=4)[CH:14]=3)=[N:7][CH:6]=[N:5][C:4]=2[S:8][CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 7366184-Chlorothieno[2,3-d]pyrimidineHCID 2763417(3-Phenyl-5-isoxazolyl)methanol

Product 1

HCID 734426745-Methyl-4-((3-phenyl-isoxazol-5-yl)-methoxy-)-thieno[2,3-d]pyrimidine

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent2×

Procedure

0.184 g (1 mmol) of 4-chloro-thieno[2,3-d]pyrimidine was dissolved in 5 ml of dry isopropanol. A solution of 0.175 g (1 mmol) of 5-hydroxymethyl-3-phenyl-isoxazole in 5 ml isopropanol was slowly added dropwise into the reaction system, followed by the addition of 0.101 g (1 mmol) freshly distilled triethylamine. The system was stirred at room temperature for 30 min and then was reacted at 60. After the completion of the reaction monitored by TLC, the reaction solution was concentrated under vacuum. The residue was directly separated on (V(petroleum ether):V(ethyl acetate)=9:1-4:1) to give the target compound of 5-methyl-4-((3-phenyl-isoxazol-5-yl)-methoxy-)-thieno[2,3-d]pyrimidine (named S-1 in the following Table). The other compounds were synthesized according to the synthetic process of 5-methyl-4-((3-phenyl-isoxazol-5-yl)-methoxy-)-thieno[2,3-d]pyrimidine. Their structures were determined by analytical methods of IR, 1H NMR, ESI-MS, etc. The physical constants and spectral data of preferred compounds were illustrated in the form of table.

Workup

  1. customwas reacted at 60
  2. concentrationthe reaction solution was concentrated under vacuum
  3. customThe residue was directly separated on (V(petroleum ether):V(ethyl acetate)=9:1-4:1)

Sources & evidence

ORD record
ord-5777f72ff95242d3a6dc2f98fb9c0e37
Source dataset
uspto-grants-2016_09
Patent number
US09434741B2

Reaction notes

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