Acetonitrile → HCID 21062814, compound

HRID 1242789Notes

Reaction equation

HRID 1242789 reaction equation
ClC1N=[CH:6][C:5]2[S:8][CH:9]=[CH:10][C:4]=2N=1.C[CH2:12][N:13]([CH:17](C)C)C(C)C.[C:20]([N:27]1[CH2:32][CH2:31][NH:30][CH2:29][CH2:28]1)([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21].CC#[N:35]>>[CH3:6][C:5]1[S:8][C:9]2[N:35]=[CH:12][N:13]=[C:17]([N:30]3[CH2:29][CH2:28][N:27]([C:20]([O:22][C:23]([CH3:26])([CH3:25])[CH3:24])=[O:21])[CH2:32][CH2:31]3)[C:10]=2[CH:4]=1

Participants

5

Reactant 4

HCID 6342AcetonitrileHCID 81531DiisopropylethylamineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 455884632-Chlorothieno[3,2-d]pyrimidine

Product 1

HCID 21062814HCID 21062814, compoundYield 98%

Procedure

The title compound was obtained by mixing the material from step 3 (500 mg, 2.71 mmol) in MeCN (11 mL) at rt under argon with DIEA (1.9 mL, 11 mmol). To this solution was then added Boc-piperazine (553 mgs, 3.0 mmol). The mixture was then warmed to 80–85° C. for 1.5 hrs (followed by analytical RP-HPLC). The solvent was evaporated under reduced pressure and water (30 mL) was added. The water was washed with DCM (3-×15 mL), and the DCM was dried with MgSO4, filtered, and removed in vacuuo to afford a 98% yield of the desired product. ES-MS: (M+H)+ 335.

Workup

  1. temperatureThe mixture was then warmed to 80–85° C. for 1.5 hrs (followed by analytical RP-HPLC)
  2. customThe solvent was evaporated under reduced pressure and water (30 mL)
  3. additionwas added
  4. washThe water was washed with DCM (3-×15 mL)
  5. dry with materialthe DCM was dried with MgSO4
  6. filtrationfiltered
  7. customremoved in vacuuo

Sources & evidence

ORD record
ord-d71317b2f89349448d9d0c06dd4ff419
Source dataset
uspto-grants-2006_10
Patent number
US07115741B2

Reaction notes

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