Acetonitrile → HCID 69076461, compound

HRID 225478Notes

Reaction equation

HRID 225478 reaction equation
[Cl:1][C:2]1[C:3]2[S:19][CH:18]=[CH:17][C:4]=2[N:5]=[C:6]([C:8]2[CH:13]=[C:12]([F:14])[C:11]([Cl:15])=[CH:10][C:9]=2[F:16])[N:7]=1.C([N:23]([CH:26]([CH3:28])C)[CH2:24][CH3:25])(C)C.[C:29](#N)[CH3:30]>O>[ClH:1].[N:23]1([C:2]2[C:3]3[S:19][CH:18]=[CH:17][C:4]=3[N:5]=[C:6]([C:8]3[CH:13]=[C:12]([F:14])[C:11]([Cl:15])=[CH:10][C:9]=3[F:16])[N:7]=2)[CH2:24][CH2:25][CH2:30][CH2:29][CH2:28][CH2:26]1

Participants

5

Reactant 3

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 57753077HCID 57753077, compound

Product 1

HCID 69076461HCID 69076461, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 9.52 g of 4-chloro-2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine, 3.13 g of hexamethyleneimine, 10.50 ml of diisopropyl ethylamine and 190 ml of acetonitrile was stirred for 5 hours at 70° C. 600 ml of water was added to the reaction mixture and the precipitate was filtered, washed with water and dried at 50° C. under reduced pressure. The obtained solid was dissolved in 40 ml of THF. The solution was added to 15 ml of 4M HCl-EtOAc solution and concentrated under reduced pressure to give a solid. Through recrystallization of this solid from EtOH-ether, 10.97 g of 4-azepane-1-yl-2-(4-chloro-2,5-difluorophenyl)thieno[3,2-d]pyrimidine hydrochloride was obtained.

Workup

  1. filtrationthe precipitate was filtered
  2. washwashed with water
  3. customdried at 50° C. under reduced pressure
  4. dissolutionThe obtained solid was dissolved in 40 ml of THF
  5. additionThe solution was added to 15 ml of 4M HCl-EtOAc solution
  6. concentrationconcentrated under reduced pressure
  7. customto give a solid
  8. customThrough recrystallization of this solid from EtOH-ether

Sources & evidence

ORD record
ord-e745b5af03e84bda991a2deb5f7833d6
Source dataset
uspto-grants-2009_07
Patent number
US07557112B2

Reaction notes

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