Dichloromethane → 2-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (2,4-dimethoxy-phenyl)-amide

HRID 1773621Notes

Reaction equation

HRID 1773621 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[NH:11][C:12]([C:14]1[C:18]2[N:19]=[C:20](Cl)[N:21]=[CH:22][C:17]=2[S:16][CH:15]=1)=[O:13].[C@@H:24]1([NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]1[NH2:30].ClCCl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[CH:6]=[CH:5][C:4]=1[NH:11][C:12]([C:14]1[C:18]2[N:19]=[C:20]([NH:30][C@@H:25]3[CH2:26][CH2:27][CH2:28][CH2:29][C@@H:24]3[NH2:31])[N:21]=[CH:22][C:17]=2[S:16][CH:15]=1)=[O:13]

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 3429171,2-Diaminocyclohexane, cis-HCID 870961102-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid(2,4-dimethoxy-phenyl)-amide

Product 1

HCID 566467652-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (2,4-dimethoxy-phenyl)-amide

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.047 g (0.134 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid(2,4-dimethoxy-phenyl)-amide in 1.34 mL of dioxane was added 0.0967 mL (0.806 mmole) of (cis-cyclohexane-1,2-diamine. The mixture was heated at 100 degrees for over night. Dichloromethane was added and washed with aqueous sodium bicarbonate. The aqueous layer was washed twice with dichloromethane. The organic layer was washed with brine, dried over anhydrous sodium sulfate, filtered and concentrated under reduced pressure. Purification by silica gel chromatography, eluting with dichloromethane-0.7 N ammonia solution in methanol (gradient 100:0-90:10) gave 0.052 g of 2-(cis-2-amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (2,4-dimethoxy-phenyl)-amide as a yellow solid. MH+/Z=428

Workup

  1. temperatureThe mixture was heated at 100 degrees for over night
  2. washwashed with aqueous sodium bicarbonate
  3. washThe aqueous layer was washed twice with dichloromethane
  4. washThe organic layer was washed with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customPurification by silica gel chromatography
  9. washeluting with dichloromethane-0.7 N ammonia solution in methanol (gradient 100:0-90:10)

Sources & evidence

ORD record
ord-5a3296755c794aaea4cb32a2821db715
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

Loading…