4-Fluoro-2-(1-methylethoxy)benzenamine → N-(3-(Dimethylamino)propyl)-4-(4-fluoro-2-iso-propoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-sulfonamide

HRID 450589Notes

Reaction equation

HRID 450589 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([O:9][CH:10]([CH3:12])[CH3:11])[CH:3]=1.Cl.Cl[C:15]1[C:16]2[C:23]([CH3:24])=[C:22]([S:25]([NH:28][CH2:29][CH2:30][CH2:31][N:32]([CH3:34])[CH3:33])(=[O:27])=[O:26])[S:21][C:17]=2[N:18]=[CH:19][N:20]=1.O.[OH-].[NH4+]>O1CCOCC1.O>[CH3:34][N:32]([CH3:33])[CH2:31][CH2:30][CH2:29][NH:28][S:25]([C:22]1[S:21][C:17]2[N:18]=[CH:19][N:20]=[C:15]([NH:6][C:5]3[CH:7]=[CH:8][C:2]([F:1])=[CH:3][C:4]=3[O:9][CH:10]([CH3:12])[CH3:11])[C:16]=2[C:23]=1[CH3:24])(=[O:27])=[O:26]

Participants

6

Reactant 3

HCID 37563854-Fluoro-2-(1-methylethoxy)benzenamineHCID 86589665Water ammonium hydroxideHCID 866656674-chloro-N-(3-(dimethylamino)propyl)-5-methylthieno[2,3-d]pyrimidine-6-sulfonamide hydrochloride salt

Product 1

HCID 46182300N-(3-(Dimethylamino)propyl)-4-(4-fluoro-2-iso-propoxyphenylamino)-5-methylthieno[2,3-d]pyrimidine-6-sulfonamideYield 28.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 312751,4-DioxaneSolvent

Procedure

4-Fluoro-2-iso-propoxyaniline (0.049 g, 0.28 mmol) and 4-chloro-N-(3-(dimethylamino)propyl)-5-methylthieno[2,3-d]pyrimidine-6-sulfonamide hydrochloride salt (0.1 g, 0.28 mmol) were heated at 70° C. in anhydrous 1,4-dioxane (1.5 mL) for 4 hours. The solution was cooled to ambient temperature and diluted with water (2.0 mL) and adjusted to pH 9 (4:1 water/ammonium hydroxide solution). The precipitate was collected, washed with water and diethyl ether to yield the title compound as beige solid (0.039 g, 28%).

Workup

  1. customThe precipitate was collected
  2. washwashed with water and diethyl ether

Sources & evidence

ORD record
ord-f6a81752773b4647ac8f117f82f70229
Source dataset
uspto-grants-2013_07
Patent number
US08486953B2

Reaction notes

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