1,4-Diaminocyclohexane → 1-N-[6-(propan-2-yl)thieno[2,3-d]pyrimidin-4-yl]cyclohexane-1,4-diamine

HRID 525069Notes

Reaction equation

HRID 525069 reaction equation
Cl[C:2]1[C:3]2[CH:10]=[C:9]([CH:11]([CH3:13])[CH3:12])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:14]1([NH2:21])[CH2:19][CH2:18][CH:17]([NH2:20])[CH2:16][CH2:15]1>CN(C)C=O>[CH3:12][CH:11]([C:9]1[S:8][C:4]2[N:5]=[CH:6][N:7]=[C:2]([NH:20][CH:17]3[CH2:18][CH2:19][CH:14]([NH2:21])[CH2:15][CH2:16]3)[C:3]=2[CH:10]=1)[CH3:13]

Participants

4

Reactant 2

HCID 183741,4-DiaminocyclohexaneHCID 27576274-Chloro-6-isopropylthieno(2,3-d)pyrimidine

Product 1

HCID 681105401-N-[6-(propan-2-yl)thieno[2,3-d]pyrimidin-4-yl]cyclohexane-1,4-diamine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a 100-mL round-bottom flask was added a solution of commercially available 4-chloro-6-(propan-2-yl)thieno[2,3-d]pyrimidine (3 g, 14.10 mmol, 1.00 equiv) in N,N-dimethylformamide (30 mL), TEA (4.3 g, 42.49 mmol, 3.01 equiv), and cyclohexane-1,4-diamine (9.6 g, 84.07 mmol, 5.96 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 100 mL of water. The resulting solution was extracted with 3×100 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 3×100 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 3.5 g (85%) of 1-N-[6-(propan-2-yl)thieno[2,3-d]pyrimidin-4-yl]cyclohexane-1,4-diamine as a yellow oil.

Workup

  1. customThe reaction was then quenched by the addition of 100 mL of water
  2. extractionThe resulting solution was extracted with 3×100 mL of ethyl acetate
  3. washThe resulting mixture was washed with 3×100 mL of brine
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 3.5 g (85%) of 1-N-[6-(propan-2-yl)thieno[2,3-d]pyrimidin-4-yl]cyclohexane-1,4-diamine as a yellow oil

Sources & evidence

ORD record
ord-546c1734c1774ffa88272b34599be3c4
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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