Formaldehyde → HCID 57832661, compound

HRID 729542Notes

Reaction equation

HRID 729542 reaction equation
[CH:1]12[CH2:7][CH:4]([NH:5][CH2:6]1)[CH2:3][N:2]2[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[CH:19]=2)[N:9]=1.C=O.[BH3-][C:36]#N.[Na+].C([O-])(O)=O.[Na+]>C(Cl)(Cl)Cl.CO>[CH3:36][N:5]1[CH2:6][CH:1]2[CH2:7][CH:4]1[CH2:3][N:2]2[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[N:11]=[C:10]([C:18]2[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C@H:25]([C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)[CH3:26])[CH:19]=2)[N:9]=1

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 516892Sodium BicarbonateHCID 5003444Sodium cyanoborohydrideHCID 57832668HCID 57832668, compound

Product 1

HCID 57832661HCID 57832661, compound

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent

Procedure

To a solution of (S)-{4-[4-(2,5-diazabicyclo[2.2.1]hept-2-yl)quinazolin-2-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine (105 mg, 0.25 mmol) in 2 mL of CHCl3 at RT was added formaldehyde (37%, 407 μL, 5.00 mmol), NaCNBH3 (47 mg, 0.75 mmol) and MeOH (0.4 mL). The reaction stirred at RT overnight and then NaHCO3 (sat.) was added and the product was extracted with CH2Cl2. The combined organic layers were dried over Na2SO4, filtered and concentrated. The crude product was purified by silica gel chromatography (gradient elution 1 to 5% MeOH in CH2Cl2) to give (S)-{4-[4-(5-methyl-2,5-diaza-bicyclo[2.2.1]hept-2-yl)-quinazolin-2-yl]-pyridin-2-yl}-(1-phenyl-ethyl)-amine as a pale yellow solid. MS (ES+): 437 (M+H)+.

Workup

  1. extractionthe product was extracted with CH2Cl2
  2. dry with materialThe combined organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe crude product was purified by silica gel chromatography (gradient elution 1 to 5% MeOH in CH2Cl2)

Sources & evidence

ORD record
ord-1be614f3b415402c8ef7c34f2c3a8c55
Source dataset
uspto-grants-2009_09
Patent number
US07582631B2

Reaction notes

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