Chloroform → 4-Chloro-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-2-amine

HRID 2172896Notes

Reaction equation

HRID 2172896 reaction equation
[NH2:1][C:2]1[NH:3][C:4](=O)[C:5]2[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=3[S:8][C:6]=2[N:7]=1.O=P(Cl)(Cl)[Cl:18].C(Cl)(Cl)Cl.CCCCCC>C(OC(=O)C)(=O)C>[Cl:18][C:4]1[C:5]2[C:10]3[CH2:11][CH2:12][CH2:13][CH2:14][C:9]=3[S:8][C:6]=2[N:7]=[C:2]([NH2:1])[N:3]=1

Participants

6

Reactant 4

HCID 6212ChloroformHCID 8058HexaneHCID 24813Phosphorus oxychlorideHCID 2901972-Amino-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-4(3h)-one

Product 1

HCID 129102004-Chloro-5,6,7,8-tetrahydro[1]benzothieno[2,3-d]pyrimidin-2-amineYield 44%

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

To a 50 mL flask was added 10 (221 mg, 1 mmol) and 10 mL POCl3. The resulting mixture was refluxed for 2 h, and the solvent was removed under reduced pressure to afford a dark residue. To this was added 30 mL of CHCl3 and 300 mg of silica gel. The solvent was evaporated to afford a plug. Column chromatography of the plug with hexane: acetyl acetate=20:1 as eluent afford 105 mg (44%) of 11 as a yellow solid:

Workup

  1. temperatureThe resulting mixture was refluxed for 2 h
  2. customthe solvent was removed under reduced pressure
  3. customto afford a dark residue
  4. customThe solvent was evaporated
  5. customto afford a plug

Sources & evidence

ORD record
ord-4357a1e6bed444b79c90c45b72e89348
Source dataset
uspto-grants-2015_06
Patent number
US09056869B2

Reaction notes

Loading…