Water → HCID 62313850, compound

HRID 525082Notes

Reaction equation

HRID 525082 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([CH2:11][CH3:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:13]1([NH2:20])[CH2:18][CH2:17][CH:16]([NH2:19])[CH2:15][CH2:14]1.C(N(CC)CC)C.O>CN(C)C=O>[CH2:11]([C:9]1[S:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:19][CH:16]3[CH2:17][CH2:18][CH:13]([NH2:20])[CH2:14][CH2:15]3)[C:3]=2[CH:10]=1)[CH3:12]

Participants

6

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 183741,4-DiaminocyclohexaneHCID 9161764-chloro-6-ethylthieno[2,3-d]pyrimidine

Product 1

HCID 62313850HCID 62313850, compoundYield 107.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Into a 50-mL round-bottom flask, was placed 4-chloro-6-ethylthieno[2,3-d]pyrimidine (200 mg, 1.01 mmol, 1.00 equiv), cyclohexane-1,4-diamine (600 mg, 5.25 mmol, 5.22 equiv) in anhydrous N,N-dimethylformamide (5 mL) at room temperature. Then triethylamine (300 mg, 2.96 mmol, 2.95 equiv) was added via syringe and the resulting solution was stirred overnight at ambient temperature. After completion of the reaction, the resulting solution was diluted H2O, extracted with 3×30 mL of ethyl acetate. The combined organic layers were washed with brine, dried over anhydrous sodium sulfate and concentrated under vacuum. This desired 1-N-[6-ethylthieno[2,3-d]pyrimidin-4-yl]cyclohexane-1,4-diamine (0.3 g, crude) was obtained as a off-white solid which was used for next step without further purification.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. customat room temperature
  3. customAfter completion of the reaction
  4. extractionextracted with 3×30 mL of ethyl acetate
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-0335e33e4eb64b1f9599999e2733e5f9
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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