Phosphorus oxychloride → 4-chloro-N-(3-(dimethylamino)propyl)-5-methylthieno[2,3-d]pyrimidine-6-sulfonamide hydrochloride salt

HRID 450588Notes

Reaction equation

HRID 450588 reaction equation
[CH3:1][N:2]([CH3:21])[CH2:3][CH2:4][CH2:5][NH:6][S:7]([C:10]1[S:19][C:13]2[N:14]=[CH:15][NH:16][C:17](=O)[C:12]=2[C:11]=1[CH3:20])(=[O:9])=[O:8].P(Cl)(Cl)([Cl:24])=O>>[ClH:24].[Cl:24][C:17]1[C:12]2[C:11]([CH3:20])=[C:10]([S:7]([NH:6][CH2:5][CH2:4][CH2:3][N:2]([CH3:21])[CH3:1])(=[O:9])=[O:8])[S:19][C:13]=2[N:14]=[CH:15][N:16]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 69669093HCID 69669093, compound

Product 1

HCID 866656674-chloro-N-(3-(dimethylamino)propyl)-5-methylthieno[2,3-d]pyrimidine-6-sulfonamide hydrochloride salt

Procedure

To N-(3-(dimethylamino)propyl)-5-methyl-4-oxo-3,4-dihydrothieno[2,3-d]pyrimidine-6-sulfonamide (0.6 g, 1.8 mmol) was added phosphorus oxychloride (5.0 mL, 36 mmol) and the suspension heated at reflux for 1.5 hours. The reaction was cooled to ambient temperature and the excess phosphorus oxychloride removed under vacuum. The residue was co-evaporated several times with chloroform. Drying under vacuum gave a hydroscopic cream solid that was used without further purification (0.65 g, 92%).

Workup

  1. temperaturethe suspension heated
  2. temperatureat reflux for 1.5 hours
  3. customthe excess phosphorus oxychloride removed under vacuum
  4. customDrying under vacuum
  5. customgave a hydroscopic cream solid that
  6. customwas used without further purification (0.65 g, 92%)

Sources & evidence

ORD record
ord-c2872b3eba1e4f8ea82a1490421cd450
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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