Diethyl Ether → HCID 9868218, compound

HRID 854337Notes

Reaction equation

HRID 854337 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:5][NH:6][C:7]1[C:8]2[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[S:15][C:9]=2[N:10]=[C:11]([CH2:13]Cl)[N:12]=1.[NH2:27][CH2:28][CH2:29][CH2:30][OH:31].CCOCC.C1(N)C(F)=C(F)C(F)=C(N)C=1F.Cl.Cl>CN(C=O)C.O.Cl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:22]=[CH:23][C:24]=1[O:25][CH3:26])[CH2:5][NH:6][C:7]1[C:8]2[C:17]3[CH2:18][CH2:19][CH2:20][CH2:21][C:16]=3[S:15][C:9]=2[N:10]=[C:11]([CH2:13][NH:27][CH2:28][CH2:29][CH2:30][OH:31])[N:12]=1

Participants

8

Reactant 4

HCID 3283Diethyl EtherHCID 90863-Amino-1-propanolHCID 149026Tetrafluoro-m-phenylenediamine dihydrochlorideHCID 15552197HCID 15552197, compound

Product 1

HCID 9868218HCID 9868218, compound

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2 g of 4-(3-chloro-4-methoxybenzylamino)-2-chloromethyl-5,6,7,8 tetrahydrobenzothieno[2,3-d]pyrimidine in 10 ml of DMF is treated with 5 ml of 3-aminopropanol and heated at 80° for one hour. It is then diluted with water and extracted with ethyl acetate. The crystalline product obtained after customary work-up is dissolved in alcoholic HCl and treated with ether until turbidity. 2.1 g of 4-(3-chloro-4-methoxybenzylamino)-2-(3-hydroxypropylaminomethyl)-5,6,7,8-tetrahydrobenzothieno[2,3-d]pyrimidine are obtained in the form of its dihydrochloride.

Workup

  1. temperatureheated at 80° for one hour
  2. extractionextracted with ethyl acetate
  3. customThe crystalline product obtained after customary work-up

Sources & evidence

ORD record
ord-21398076ede04b6da7daa2a742ecca79
Source dataset
uspto-grants-2007_08
Patent number
US07259168B2

Reaction notes

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