Triethylamine → 6-(4-(1-benzhydrylazetidin-3-yl)piperazin-1-yl)-3-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine

HRID 68722Notes

Reaction equation

HRID 68722 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)[N:9]=[C:10]([CH2:11][CH3:12])[C:5]2=[CH:4][N:3]=1.[CH:19]([N:32]1[CH2:35][CH:34]([N:36]2[CH2:41][CH2:40][NH:39][CH2:38][CH2:37]2)[CH2:33]1)([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.C(N(CC)CC)C>>[CH:19]([N:32]1[CH2:35][CH:34]([N:36]2[CH2:41][CH2:40][N:39]([C:2]3[N:7]=[C:6]4[N:8]([C:13]5[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=5)[N:9]=[C:10]([CH2:11][CH3:12])[C:5]4=[CH:4][N:3]=3)[CH2:38][CH2:37]2)[CH2:33]1)([C:20]1[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 16123292HCID 16123292, compoundHCID 86658773HCID 86658773, compound

Product 1

HCID 674479546-(4-(1-benzhydrylazetidin-3-yl)piperazin-1-yl)-3-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine

Procedure

Into a 100-mL 3-necked round-bottom flask, was placed a solution of 6-chloro-3-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine (420 mg, 1.63 mmol, 1.00 equiv) in C7H8 (15 mL) at room temperature. To the resulting mixture was then added 1-(1-benzhydrylazetidin-3-yl)piperazine (500 mg, 1.63 mmol, 1.00 equiv), in portions at room temperature, followed by triethylamine (490 mg, 4.85 mmol, 3.00 equiv), in portions at room temperature. The resulting solution was heated to reflux overnight. The resulting mixture was concentrated under vacuum. The residue was dissolved in DCM (20 mL). The resulting mixture was washed with sodium chloride (2×15 mL). The resulting mixture was concentrated under vacuum. The resulting mixture was washed with methanol (1×5 mL). The solids were collected by filtration to yield 6-(4-(1-benzhydrylazetidin-3-yl)piperazin-1-yl)-3-ethyl-1-phenyl-1H-pyrazolo[3,4-d]pyrimidine as a yellow solid. MS (m/z): 530 [MH+].

Workup

  1. customInto a 100-mL 3-necked round-bottom flask, was placed
  2. customat room temperature
  3. customat room temperature
  4. temperatureThe resulting solution was heated
  5. temperatureto reflux overnight
  6. concentrationThe resulting mixture was concentrated under vacuum
  7. dissolutionThe residue was dissolved in DCM (20 mL)
  8. washThe resulting mixture was washed with sodium chloride (2×15 mL)
  9. concentrationThe resulting mixture was concentrated under vacuum
  10. washThe resulting mixture was washed with methanol (1×5 mL)
  11. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-0337da89efcb4a19b365d169c260bfe5
Source dataset
uspto-grants-2014_09
Patent number
US08822447B2

Reaction notes

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