Acetic Acid → HCID 66733570, compound

HRID 2047204Notes

Reaction equation

HRID 2047204 reaction equation
[CH3:1][Si:2]([CH3:38])([CH3:37])[CH2:3][CH2:4][O:5][CH2:6][N:7]([CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:36])([CH3:35])[CH3:34])[C:8]1[N:13]2[N:14]=[CH:15][C:16]([C:17]3[CH:18]=[N:19][C:20]4[C:25]([CH:26]=3)=[CH:24][CH:23]=[CH:22][CH:21]=4)=[C:12]2[N:11]=[C:10]([CH:27]=O)[CH:9]=1.[NH:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1.CC(O)=O.[BH3-]C#N.[Na+]>CCO>[O:42]1[CH2:43][CH2:44][N:39]([CH2:27][C:10]2[CH:9]=[C:8]([N:7]([CH2:6][O:5][CH2:4][CH2:3][Si:2]([CH3:1])([CH3:37])[CH3:38])[CH2:29][O:30][CH2:31][CH2:32][Si:33]([CH3:35])([CH3:34])[CH3:36])[N:13]3[N:14]=[CH:15][C:16]([C:17]4[CH:18]=[N:19][C:20]5[C:25]([CH:26]=4)=[CH:24][CH:23]=[CH:22][CH:21]=5)=[C:12]3[N:11]=2)[CH2:40][CH2:41]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 5003444Sodium cyanoborohydrideHCID 86664790HCID 86664790, compound

Product 1

HCID 66733570HCID 66733570, compoundYield 107.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

To 7-(bis((2-(trimethylsilyl)ethoxy)methyl)amino)-3-(quinolin-3-yl)pyrazolo[1,5-a]pyrimidine-5-carbaldehyde (0.15 g, 0.3 mmol) in EtOH (10 mL) was added morpholine (0.12 mL, 1.4 mmol) and AcOH (0.2 mL), and the resulting mixture was stirred at room temperature for 15 minutes. NaBH3CN (0.12 g, 2.0 mmol) in EtOH (1.5 mL total) was then added and the reaction mixture was stirred at room temperature for 16 hours, at which time LC/MS analysis confirmed full consumption of starting material. Saturated NaHCO3 solution (˜20 mL) was added and the mixture was stirred for 30 minutes. The mixture was transferred to a separatory funnel with CH2Cl2 (30 mL) and H2O (10 mL) and brine (20 mL) was then added. Organics were extracted with CH2Cl2 (4×30 mL), dried (Na2SO4) and concentrated in vacuo to give crude 5-(morpholinomethyl)-3-(quinolin-3-yl)-N,N-bis((2-(trimethylsilyl)ethoxy)methyl)pyrazolo[1,5-a]pyrimidin-7-amine as a brown oil (0.2 g). LCMS: 2.01 mins, m/z=621.3 (MH+).

Workup

  1. stirringthe reaction mixture was stirred at room temperature for 16 hours, at which time LC/MS analysis
  2. customconsumption of starting material
  3. additionSaturated NaHCO3 solution (˜20 mL) was added
  4. stirringthe mixture was stirred for 30 minutes
  5. customThe mixture was transferred to a separatory funnel with CH2Cl2 (30 mL) and H2O (10 mL) and brine (20 mL)
  6. additionwas then added
  7. extractionOrganics were extracted with CH2Cl2 (4×30 mL)
  8. dry with materialdried (Na2SO4)
  9. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-921ccba5a9a542248b1437ad59178b3c
Source dataset
uspto-grants-2013_11
Patent number
US08591943B2

Reaction notes

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