Phosphorus oxychloride → 4-chloro-9H-pyrimido(4,5-b)indole

HRID 1916281Notes

Reaction equation

HRID 1916281 reaction equation
[N:1]1[C:6]2[NH:7][C:8]3[C:13]([C:5]=2[C:4](=O)[NH:3][CH:2]=1)=[CH:12][CH:11]=[CH:10][CH:9]=3.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:4]1[C:5]2[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[NH:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1354360363H,4H,9H-pyrimido[4,5-b]indol-4-one

Product 1

HCID 58064084-chloro-9H-pyrimido(4,5-b)indole

Procedure

A suspension of 3H-pyrimido[4,5-b]indol-4(9H)-one (0.091 g, 0.491 mmol) in phosphorous oxychloride (8 mL) was refluxed under nitrogen for 24 hours. Phosphorous oxychloride was removed by evaporation and the residue was partitioned between water (20 mL) and chloroform (2×20 mL). The organic extracts were filtered through celite, dried (Na2SO4) and concentrated to give 4-chloro-9H-pyrimido[4,5-b]indole as a yellow solid (0.103 g, 0.50 mmol, quantitative). 1H NMR (500 MHz, CDCl3) δ 7.60 (1H, dd, J=8.8 Hz), 7.70 (1H, dd, J=8.8 Hz), 8.43 (1H, d, J=8 Hz), 8.52 (1H, d, J=8 Hz), 8.98 (1H, s); LC-MS (3) Rt: 5.59 min; m/z (ESI) 206, 204 [MH+].

Workup

  1. temperaturewas refluxed under nitrogen for 24 hours
  2. customPhosphorous oxychloride was removed by evaporation
  3. customthe residue was partitioned between water (20 mL) and chloroform (2×20 mL)
  4. filtrationThe organic extracts were filtered through celite
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-b1205de7097846d7925c7150108df859
Source dataset
uspto-grants-2013_12
Patent number
US08618121B2

Reaction notes

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