Sodium Bicarbonate → HCID 90053325, compound

HRID 2284735Notes

Reaction equation

HRID 2284735 reaction equation
O=[CH:2][CH2:3][CH2:4][C:5]#[C:6][C:7]1[C:8]([NH:22][CH2:23][CH2:24][CH3:25])=[N:9][C:10]([NH:13][C:14]2[CH:21]=[CH:20][C:17]([C:18]#[N:19])=[CH:16][CH:15]=2)=[N:11][CH:12]=1.[NH2:26][C:27]([CH3:39])([CH3:38])[CH2:28][N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:35])([CH3:34])[CH3:33].C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)([O-])O.[Na+]>C(Cl)Cl.C(OCC)(=O)C.C(O)(=O)C>[C:18]([C:17]1[CH:20]=[CH:21][C:14]([NH:13][C:10]2[N:9]=[C:8]([NH:22][CH2:23][CH2:24][CH3:25])[C:7]([C:6]#[C:5][CH2:4][CH2:3][CH2:2][NH:26][C:27]([CH3:39])([CH3:38])[CH2:28][N:29]([CH3:37])[C:30](=[O:36])[O:31][C:32]([CH3:33])([CH3:34])[CH3:35])=[CH:12][N:11]=2)=[CH:15][CH:16]=1)#[N:19]

Participants

8

Reactant 4

HCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 84014952HCID 84014952, compoundHCID 90051763HCID 90051763, compound

Product 1

HCID 90053325HCID 90053325, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 4-((5-(5-oxo-1-pentyn-1-yl)-4-(propylamino)pyrimidin-2-yl)amino)benzonitrile (G12, 300 mg) and tert-butyl (2-amino-2-methylpropyl)(methyl)carbamate (G10, 112 mg) in methylene chloride (4 mL), sodium triacetoxyborohydride (195 mg) and acetic acid (21 μL) were added at room temperature, and the mixture was stirred at the same temperature for 3 hours. To the reaction mixture, ethyl acetate and saturated aqueous sodium hydrogencarbonate were added. The organic layer was separated, washed with saturated aqueous sodium chloride, and then dried over anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography (eluent, 100 to 80% ethyl acetate in methanol) to obtain tert-butyl (2-((5-(2-((4-cyanophenyl)amino)-4-(propylamino)pyrimidin-5-yl)-4-pentyn-1-yl)amino)-2-methylpropyl)(methyl)carbamate (G13, 80 mg).

Workup

  1. customThe organic layer was separated
  2. washwashed with saturated aqueous sodium chloride
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe obtained residue was purified by silica gel column chromatography (eluent, 100 to 80% ethyl acetate in methanol)

Sources & evidence

ORD record
ord-f6d80c7d8e784e8a838442d6b1ab846a
Source dataset
uspto-grants-2015_09
Patent number
US09145415B2

Reaction notes

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