1,4-Diaminocyclohexane → HCID 68110434, compound

HRID 525074Notes

Reaction equation

HRID 525074 reaction equation
Cl[C:2]1[C:3]2[C:10]([C:11]3[CH:16]=[CH:15][CH:14]=[CH:13][N:12]=3)=[CH:9][S:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH:17]1([NH2:24])[CH2:22][CH2:21][CH:20]([NH2:23])[CH2:19][CH2:18]1>CN(C)C=O>[N:12]1[CH:13]=[CH:14][CH:15]=[CH:16][C:11]=1[C:10]1[C:3]2[C:2]([NH:23][CH:20]3[CH2:21][CH2:22][CH:17]([NH2:24])[CH2:18][CH2:19]3)=[N:7][CH:6]=[N:5][C:4]=2[S:8][CH:9]=1

Participants

4

Reactant 2

HCID 183741,4-DiaminocyclohexaneHCID 86673333HCID 86673333, compound

Product 1

HCID 68110434HCID 68110434, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A 100-mL round-bottom flask was charged with 2-[4-chlorothieno[2,3-d]pyrimidin-5-yl]pyridine (1.0 g, 4.04 mmol, 1.00 equiv), N,N-dimethylformamide (10 mL), TEA (1.2 g, 11.86 mmol, 2.94 equiv) and cyclohexane-1,4-diamine (2.8 g, 24.52 mmol, 6.07 equiv). The resulting solution was stirred overnight at room temperature. The reaction was then quenched by the addition of 50 mL of water. The resulting solution was extracted with 4×50 mL of ethyl acetate and the organic layers combined. The resulting mixture was washed with 4×50 mL of brine. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.9 g (69%) of 1-N-[5-(pyridin-2-yl)thieno[2,3-d]pyrimidin-4-yl]cyclohexane-1,4-diamine as yellow oil. MS: m/z 326 (M+H)+.

Workup

  1. customThe reaction was then quenched by the addition of 50 mL of water
  2. extractionThe resulting solution was extracted with 4×50 mL of ethyl acetate
  3. washThe resulting mixture was washed with 4×50 mL of brine
  4. dry with materialThe mixture was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 0.9 g (69%) of 1-N-[5-(pyridin-2-yl)thieno[2,3-d]pyrimidin-4-yl]cyclohexane-1,4-diamine as yellow oil

Sources & evidence

ORD record
ord-e91cafcea74a45f5bfb21f13ecd81c5a
Source dataset
uspto-grants-2016_05
Patent number
US09340554B2

Reaction notes

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