Phosphorus oxychloride → 7-(4-Chlorothieno[2,3-d]pyrimidin-5-yl)-2-phenylquinoline

HRID 230239Notes

Reaction equation

HRID 230239 reaction equation
[C:1]1([C:7]2[CH:16]=[CH:15][C:14]3[C:9](=[CH:10][C:11]([C:17]4[C:25]5[C:24](=O)[NH:23][CH:22]=[N:21][C:20]=5[S:19][CH:18]=4)=[CH:12][CH:13]=3)[N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=P(Cl)(Cl)[Cl:29]>>[Cl:29][C:24]1[C:25]2[C:17]([C:11]3[CH:10]=[C:9]4[C:14]([CH:15]=[CH:16][C:7]([C:1]5[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=5)=[N:8]4)=[CH:13][CH:12]=3)=[CH:18][S:19][C:20]=2[N:21]=[CH:22][N:23]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 577623885-(2-phenylquinolin-7-yl)-3H-thieno[2,3-d]pyrimidin-4-one

Product 1

HCID 577623927-(4-Chlorothieno[2,3-d]pyrimidin-5-yl)-2-phenylquinoline

Conditions

Temperature
110 °C

Procedure

A mixture of 5-(2-phenylquinolin-7-yl)-3H-thieno[2,3-d]pyrimidin-4-one (30 mg, max. 0.084 mmol, 77% purity) and POCl3 (1.0 ml) was stirred at 110° C. for 1 h under N2. The excess POCl3 was removed in vacuo, and the residue was basified by cold NH3 (2M in isopropanol). The precipitate that was formed was filtered off. The filtrate [crude 7-(4-chlorothieno[2,3-d]pyrimidin-5-yl)-2-phenylquinoline] was used without further purification for the next step. MS (ES+): 374.2/376.2 (M/M+2). HPLC: tR=6.8 min (MicromassZQ, polar—15 min).

Workup

  1. customThe excess POCl3 was removed in vacuo
  2. customThe precipitate that was formed
  3. filtrationwas filtered off
  4. customThe filtrate [crude 7-(4-chlorothieno[2,3-d]pyrimidin-5-yl)-2-phenylquinoline] was used without further purification for the next step
  5. customHPLC: tR=6.8 min (MicromassZQ, polar—15 min)

Sources & evidence

ORD record
ord-dd2162aa715b40ba83904e217c36fba9
Source dataset
uspto-grants-2009_07
Patent number
US07566721B2

Reaction notes

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