Water → 2-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethoxy-pyridin-2-yl)-amide

HRID 1773623Notes

Reaction equation

HRID 1773623 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]([C:14]2[C:18]3[N:19]=[C:20](Cl)[N:21]=[CH:22][C:17]=3[S:16][CH:15]=2)=[O:13])=[N:7][C:8]=1[O:9][CH3:10].[C@@H:24]1([NH2:31])[CH2:29][CH2:28][CH2:27][CH2:26][C@@H:25]1[NH2:30].O.ClCCl>O1CCOCC1>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]([NH:11][C:12]([C:14]2[C:18]3[N:19]=[C:20]([NH:30][C@@H:25]4[CH2:26][CH2:27][CH2:28][CH2:29][C@@H:24]4[NH2:31])[N:21]=[CH:22][C:17]=3[S:16][CH:15]=2)=[O:13])=[N:7][C:8]=1[O:9][CH3:10]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 3429171,2-Diaminocyclohexane, cis-HCID 866613782-Chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethoxy-pyridin-2-yl)-amide

Product 1

HCID 566467642-(cis-2-Amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethoxy-pyridin-2-yl)-amideYield 48.1%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To a solution of 0.0817 g (0.233 mmole) 2-chloro-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethoxy-pyridin-2-yl)-amide in 2.33 mL of dioxane was added 0.168 mL (1.4 mmole) of cis-cyclohexane-1,2-diamine. The mixture was heated at 100 degrees for over night. Water and dichloromethane were added, separated. The aqueous layer was washed with dichloromethane twice. The organic layer was washed with aqueous sodium carbonate, 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 0.048 g of 2-(cis-2-amino-cyclohexylamino)-thieno[3,2-d]pyrimidine-7-carboxylic acid (5,6-dimethoxy-pyridin-2-yl)-amide as a light yellow solid. MH+/Z=429.

Workup

  1. temperatureThe mixture was heated at 100 degrees for over night
  2. customseparated
  3. washThe aqueous layer was washed with dichloromethane twice
  4. washThe organic layer was washed with aqueous sodium carbonate, 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-d29b86af65614d84b33cb47e97241a7b
Source dataset
uspto-grants-2016_02
Patent number
US09255110B2

Reaction notes

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