6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-2-(4-nitrophenyl)-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine → HCID 66750639, compound

HRID 75455Notes

Reaction equation

HRID 75455 reaction equation
[CH:1]12[N:8]([C:9]3[N:14]=[C:13]([C:15]4[CH:20]=[CH:19][C:18]([N+:21]([O-])=O)=[CH:17][CH:16]=4)[N:12]=[C:11]([NH:24][CH:25]4[CH2:30][CH2:29][O:28][CH2:27][CH2:26]4)[CH:10]=3)[CH:5]([CH2:6][CH2:7]1)[CH2:4][O:3][CH2:2]2>ClCCl.CC(O)C.[Pd]>[NH2:21][C:18]1[CH:17]=[CH:16][C:15]([C:13]2[N:12]=[C:11]([NH:24][CH:25]3[CH2:30][CH2:29][O:28][CH2:27][CH2:26]3)[CH:10]=[C:9]([N:8]3[CH:1]4[CH2:7][CH2:6][CH:5]3[CH2:4][O:3][CH2:2]4)[N:14]=2)=[CH:20][CH:19]=1

Participants

5

Reactant 1

HCID 667505476-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-2-(4-nitrophenyl)-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine

Product 1

HCID 66750639HCID 66750639, compoundYield 91%

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 3776IsopropanolSolventHCID 6344DichloromethaneSolvent2×

Procedure

In a 250 mL round bottom flask was placed 6-(3-oxa-8-azabicyclo[3.2.1]octan-8-yl)-2-(4-nitrophenyl)-N-(tetrahydro-2H-pyran-4-yl)pyrimidin-4-amine (82 mg, 0.199 mmol) in dichloromethane (7 mL) and 2-propanol (7 mL). A catalytic amount of palladium on charcoal (wet) was added and the mixture was stirred under a hydrogen atmosphere for 16 hours. The mixture was diluted with dichloromethane, filtered over Celite™ and concentrated to give 69 mg (0.18 mmol, 91%) of a tan solid. HRMS: 382.2236 [M+H]+. For [M+H]+ mass error=−0.1 mDa or −0.35 ppm.

Workup

  1. customIn a 250 mL round bottom flask was placed
  2. filtrationfiltered over Celite™
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-0e8d1846439643e6be52ef3cc0738d8f
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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