3,3-Dimethylbutanal → {6-[1-(3,3-Dimethyl-butyl)-piperidin-4-yloxy]-5-nitro-pyrimidin-4-yl}-(4-methanesulfonyl-phenyl)-amine

HRID 2377870Notes

Reaction equation

HRID 2377870 reaction equation
[CH3:1][S:2]([C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]2[C:17]([N+:18]([O-:20])=[O:19])=[C:16]([O:21][CH:22]3[CH2:27][CH2:26][NH:25][CH2:24][CH2:23]3)[N:15]=[CH:14][N:13]=2)=[CH:7][CH:6]=1)(=[O:4])=[O:3].[CH3:28][C:29]([CH3:34])([CH3:33])[CH2:30][CH:31]=O.[BH4-].[Na+]>CO>[CH3:28][C:29]([CH3:34])([CH3:33])[CH2:30][CH2:31][N:25]1[CH2:26][CH2:27][CH:22]([O:21][C:16]2[N:15]=[CH:14][N:13]=[C:12]([NH:11][C:8]3[CH:9]=[CH:10][C:5]([S:2]([CH3:1])(=[O:4])=[O:3])=[CH:6][CH:7]=3)[C:17]=2[N+:18]([O-:20])=[O:19])[CH2:23][CH2:24]1

Participants

5

Reactant 3

HCID 763353,3-DimethylbutanalHCID 4311764Sodium borohydrideHCID 11257886(4-Methanesulfonyl-phenyl)-[5-nitro-6-(piperidin-4-yloxy)-pyrimidin-4-yl]-amine

Product 1

HCID 11202380{6-[1-(3,3-Dimethyl-butyl)-piperidin-4-yloxy]-5-nitro-pyrimidin-4-yl}-(4-methanesulfonyl-phenyl)-amine

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Compound A2 (0.20 mmol, 80 mg), and 3,3-dimethyl-butyraldehyde (0.24 mmol, 30 PL) were dissolved in methanol (2 mL) and stirred for 5 minutes at room temperature. Then, added sodium borohydride (0.25 mmol, 8.7 mg) and stirred for 10 minutes at room temperature. The reaction mixture was quenched with saturated ammonium chloride solution (1 mL) followed by an extraction with dichloromethane. Removal of organic solvent in vacuo and purification by prep-LCMS provided Compound A7 as a yellow solid (12 mg, 13%). 1H NMR (400 MHz, CDCl3) δ (ppm): 10.17 (s, 1H), 8.36 (s, 1H), 7.90 (d, 2H), 7.78 (d, 2H), 5.71 (s broad, 1H), 3.51 (d, 2H), 3.08 (m, 2H), 2.97 (m, 5H), 2.38 (m, 2H), 2.14 (m, 2H), 1.60 (m, 2H), 0.85 (s, 9H). LCMS (ESI), m/z 478.3 (M+H+, 100%).

Workup

  1. stirringstirred for 10 minutes at room temperature
  2. customThe reaction mixture was quenched with saturated ammonium chloride solution (1 mL)
  3. extractionfollowed by an extraction with dichloromethane
  4. customRemoval of organic solvent
  5. customin vacuo and purification by prep-LCMS provided Compound A7 as a yellow solid (12 mg, 13%)

Sources & evidence

ORD record
ord-a85598d436b64f2abcf9a3b4b7f05131
Source dataset
uspto-grants-2008_12
Patent number
US07470699B2

Reaction notes

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