Acetic Acid → HCID 58234054, compound

HRID 1365245Notes

Reaction equation

HRID 1365245 reaction equation
Cl[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.[CH3:19][NH:20][CH:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1.CC(O)=O.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+].CC1(C)C(C)(C)OB([C:54]2[CH:55]=[N:56][CH:57]=[CH:58][CH:59]=2)O1>ClCCCl>[CH3:19][N:20]([CH2:11][C:9]1[S:10][C:5]2[C:4]([N:13]3[CH2:18][CH2:17][O:16][CH2:15][CH2:14]3)=[N:3][C:2]([C:54]3[CH:55]=[N:56][CH:57]=[CH:58][CH:59]=3)=[N:7][C:6]=2[CH:8]=1)[CH:21]1[CH2:26][CH2:25][N:24]([CH3:27])[CH2:23][CH2:22]1

Participants

7

Reactant 5

HCID 176Acetic AcidHCID 5663231-Methyl-4-(methylamino)piperidineHCID 27346563-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 58234054HCID 58234054, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of 2-chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde (0.5 g, 1.8 mmol) in 1,2-dichloroethane (10 mL) was added N,1-dimethylpiperidin-4-amine (0.3 g, 2.3 mmol) and AcOH (100 μL, 1.8 mmol). After stirring 10 min at room temperature, Na(OAc)3BH (0.5 g, 2.1 mmol) was added and the resulting mixture stirred overnight. The reaction was quenched by the addition of saturated aqueous NaHCO3 and the organic layer was separated. The aqueous layer was extracted with CH2Cl2 and the combined organics were dried over Na2SO4, filtered, and concentrated in vacuo. The crude reaction mixture was purified by silica gel chromatography (95:5; CH2Cl2: 2 M NH3 in MeOH). A portion of the purified intermediate (0.3 mmol) was coupled following General Procedure A with 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridine to provide 213 after reverse phase HPLC purification (27 mg). MS (Q1) 439 (M)+.

Workup

  1. stirringthe resulting mixture stirred overnight
  2. customThe reaction was quenched by the addition of saturated aqueous NaHCO3
  3. customthe organic layer was separated
  4. extractionThe aqueous layer was extracted with CH2Cl2
  5. dry with materialthe combined organics were dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude reaction mixture
  9. customwas purified by silica gel chromatography (95:5; CH2Cl2: 2 M NH3 in MeOH)

Sources & evidence

ORD record
ord-435740eacb084f99a9f4cccd0ceba0a3
Source dataset
uspto-grants-2011_02
Patent number
US07888352B2

Reaction notes

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