Chlorosuccinimide → HCID 86719388, compound

HRID 2175652Notes

Reaction equation

HRID 2175652 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:16]3[C:15]([NH2:17])=[N:14][CH:13]=[N:12][C:11]=3[N:10]([C:18]3[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=3)[CH:9]=2)=[CH:4][CH:3]=1.C1C(=O)N([Cl:34])C(=O)C1>ClCCCl>[Cl:34][C:9]1[N:10]([C:18]2[CH:23]=[CH:22][C:21]([N+:24]([O-:26])=[O:25])=[CH:20][CH:19]=2)[C:11]2[N:12]=[CH:13][N:14]=[C:15]([NH2:17])[C:16]=2[C:8]=1[C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=1

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 86719389HCID 86719389, compound

Product 1

HCID 86719388HCID 86719388, compoundYield 98.2%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A suspension of 5-(4-chlorophenyl)-7-(4-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (26) (527 mg, 1.4 mmol) and NCS (289 mg, 2.2 mmol) in DCE (95.0 mL) was heated to reflux for 2 hr. The reaction was then cooled down to r.t., before it was quenched with H2O (10.0 mL). The layers were separated. Aqueous phase was extracted with DCM (15.0 mL×2). The combined organic phases were washed with brine, dried over Na2SO4 and concentrated to afford 6-chloro-5-(4-chlorophenyl)-7-(4-nitrophenyl)-7H-pyrrolo[2,3-d]pyrimidin-4-amine (27) (550 mg, 95% yield) as a red solid. LC-MS (ESI): m/z (M/M+2) 399.9/401.9.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 hr
  3. customwas quenched with H2O (10.0 mL)
  4. customThe layers were separated
  5. extractionAqueous phase was extracted with DCM (15.0 mL×2)
  6. washThe combined organic phases were washed with brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-7f6e1c40a4c34a14acf92f63fb36f733
Source dataset
uspto-grants-2015_06
Patent number
US09062058B2

Reaction notes

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