Acetic Acid → HCID 87185039, compound

HRID 2066551Notes

Reaction equation

HRID 2066551 reaction equation
[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH:11]=O)=[CH:8][C:6]=2[N:7]=1.CC(O[C:24]([N:26]([CH:28]1[CH2:33][CH2:32][NH:31][CH2:30][CH2:29]1)C)=O)(C)C.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[Cl:1][C:2]1[N:3]=[C:4]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)[C:5]2[S:10][C:9]([CH2:11][N:31]3[CH2:32][CH2:33][CH:28]([NH:26][CH3:24])[CH2:29][CH2:30]3)=[CH:8][C:6]=2[N:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 27568064-N-Boc-4-N-Methyl-aminopiperidineHCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 87185039HCID 87185039, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a stirred suspension of 2-chloro-4-morpholin-4-yl-thieno[3,2-d]pyrimidine-6-carbaldehyde (1.0 g; 3.5 mmol), 4-N-Boc-4-N-methylaminopiperidine (1.0 g; 4.7 mmol) and AcOH (0.2 mL) in 1,2-dichloroethane (25 mL) was added NaB(OAc)3H (1.0 g; 4.7 mmol). The reaction mixture was stirred at RT for 5 h upon which time it was quenched with saturated NaHCO3 solution (30 mL), diluted with H2O (50 mL) and extracted with EtOAc (200 mL). The organic layer was dried (Na2SO4) and concentrated to a yellow foam (1.84 g). This foam was dissolved in CH2Cl2 (20 mL) and treated with TFA (10 mL) at RT overnight (17 h). Volatiles were removed in vacuo, the residue was taken up in 2M HCl (30 mL) and washed with CH2Cl2 (40 mL). The aqueous layer was basified with saturated Na2CO3 solution, extracted into CH2Cl2, the organic layer separated (hydrophobic frit) and solvent evaporated to give the title compound as a pale yellow solid (1.18 g; 88%).

Workup

  1. customwas quenched with saturated NaHCO3 solution (30 mL)
  2. additiondiluted with H2O (50 mL)
  3. extractionextracted with EtOAc (200 mL)
  4. dry with materialThe organic layer was dried (Na2SO4)
  5. concentrationconcentrated to a yellow foam (1.84 g)
  6. dissolutionThis foam was dissolved in CH2Cl2 (20 mL)
  7. additiontreated with TFA (10 mL) at RT overnight (17 h)
  8. customVolatiles were removed in vacuo
  9. washwashed with CH2Cl2 (40 mL)
  10. extractionextracted into CH2Cl2
  11. customthe organic layer separated (hydrophobic frit) and solvent
  12. customevaporated

Sources & evidence

ORD record
ord-690c2c3960c04f82b7492f7021e0f03e
Source dataset
uspto-grants-2012_10
Patent number
US08293735B2

Reaction notes

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