1-Methylpiperazine → 2-(1H-Indazol-4-yl)-6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine

HRID 1689866Notes

Reaction equation

HRID 1689866 reaction equation
[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:21]4[CH2:26][CH2:25][O:24][CH2:23][CH2:22]4)[C:13]4[S:18][C:17]([CH:19]=O)=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1.[CH3:27][N:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C([O-])(O)=O.[Na+]>ClCCCl.C(Cl)Cl.C(O)(=O)C>[NH:1]1[C:9]2[C:4](=[C:5]([C:10]3[N:11]=[C:12]([N:21]4[CH2:22][CH2:23][O:24][CH2:25][CH2:26]4)[C:13]4[S:18][C:17]([CH2:19][N:31]5[CH2:32][CH2:33][N:28]([CH3:27])[CH2:29][CH2:30]5)=[CH:16][C:14]=4[N:15]=3)[CH:6]=[CH:7][CH:8]=2)[CH:3]=[N:2]1

Participants

8

Reactant 4

HCID 531671-MethylpiperazineHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 236508362-(1H-Indazol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 115324722-(1H-Indazol-4-yl)-6-(4-methyl-piperazin-1-ylmethyl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidineYield 28.2%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 176Acetic AcidSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-(1H-Indazol-4-yl)-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (91 mg, 0.26 mmol), 1-methylpiperazine (34 mg, 0.36 mmol) and acetic acid (15 uL) in 1,2-dichloroethane (2 mL) was added sodium triacetoxyborohydride (60 mg, 0.28 mmol). The reaction mixture was stirred at room temperature overnight and then basified (NaHCO3, saturated), diluted with DCM, and washed with brine. The organic layer was separated, dried (MgSO4), filtered and evaporated in vacuo. The residue was purified using flash chromatography to give the title compound (33 mg).

Workup

  1. washwashed with brine
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated in vacuo
  6. customThe residue was purified

Sources & evidence

ORD record
ord-0d7370f98cfa4867b3d225acfdb64556
Source dataset
uspto-grants-2012_04
Patent number
US08153629B2

Reaction notes

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