Phosphorus sulfide (P2S5) → (+/-)-5-(7-Chloro-1,2-dimethyl-4H-benzo[5,6]cyclohepta[1,2-d]imidazol-4-yl)-1-methyl-3,4-dihydro-4-thioxo-2(1H)-pyrimidinone

HRID 324485

Reaction equation

HRID 324485 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:16]([C:17]3[C:18](=O)[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=3)[C:10]3[N:11]=[C:12]([CH3:15])[N:13]([CH3:14])[C:9]=3[CH:8]=[CH:7][C:6]=2[CH:26]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:28]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[CH:16]([C:17]3[C:18](=[S:28])[NH:19][C:20](=[O:24])[N:21]([CH3:23])[CH:22]=3)[C:10]3[N:11]=[C:12]([CH3:15])[N:13]([CH3:14])[C:9]=3[CH:8]=[CH:7][C:6]=2[CH:26]=1

Participants

4

Reactant 2

HCID 14817Phosphorus sulfide (P2S5)HCID 22003604(+/-)-5-(7-Chloro-1,2-dimethyl-4H-benzo[5,6]cyclohepta[1,2-d]imidazol-4-yl)-1-methyl-2,4(1H,3H)-pyrimidinedione

Product 1

HCID 9864902(+/-)-5-(7-Chloro-1,2-dimethyl-4H-benzo[5,6]cyclohepta[1,2-d]imidazol-4-yl)-1-methyl-3,4-dihydro-4-thioxo-2(1H)-pyrimidinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of the product from step (iv) (0.535 g), and phosphorus pentasulphide (0.967 g) in 1,4-dioxane (10 ml) was heated at 100° C. for 3 h. The solvent evaporated and the residue dissolved in dichloromethane, washed with saturated aqueous sodium bicarbonate solution then with water, dried (MgSO4) and evaporated. Purification was by chromatography on a biotage silica column, using 3% methanol/0.1% 0.880 ammonia in dichloromethane as eluant.

Workup

  1. customThe solvent evaporated
  2. dissolutionthe residue dissolved in dichloromethane
  3. washwashed with saturated aqueous sodium bicarbonate solution
  4. dry with materialwith water, dried (MgSO4)
  5. customevaporated
  6. customPurification

Sources & evidence

ORD record
ord-8d5bc3205c97433d978de526e17fa292
Source dataset
uspto-grants-2001_04
Patent number
US06218376B1

Linked notes

Loading…