Acetic Acid → HCID 58233978, compound

HRID 390927Notes

Reaction equation

HRID 390927 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]=[CH:56][C:57]([NH2:60])=[N: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:59]=[N:58][C:57]([NH2:60])=[CH:56][CH:55]=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 27565555-(4,4,5,5-Tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amineHCID 5049666Sodium triacetoxyborohydrideHCID 457899852-Chloro-4-morpholinothieno[3,2-d]pyrimidine-6-carbaldehyde

Product 1

HCID 58233978HCID 58233978, 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 5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridin-2-amine to provide 214 after reverse phase HPLC purification (25 mg). MS (Q1) 454 (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-8666827e590d4de4b7e0ce5f6e9604ff
Source dataset
uspto-grants-2013_02
Patent number
US08383620B2

Reaction notes

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