HCID 178526829, compound → HCID 178508036, compound

HRID 2356257Notes

Reaction equation

HRID 2356257 reaction equation
[CH:1]1([NH:6][C:7]2[C:12]([N+:13]([O-])=O)=[CH:11][N:10]=[C:9]([NH:16][C@H:17]3[CH2:22][CH2:21][C@H:20]([OH:23])[CH2:19][CH2:18]3)[N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1>CCO.[Pd]>[NH2:13][C:12]1[C:7]([NH:6][CH:1]2[CH2:5][CH2:4][CH2:3][CH2:2]2)=[N:8][C:9]([NH:16][C@H:17]2[CH2:18][CH2:19][C@H:20]([OH:23])[CH2:21][CH2:22]2)=[N:10][CH:11]=1

Participants

4

Reactant 1

HCID 178526829HCID 178526829, compound

Product 1

HCID 178508036HCID 178508036, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 23938PalladiumSolvent

Procedure

4-{[4-(Cyclopentylamino)-5-nitropyrimidin-2-yl]amino}trans-cyclohexan-1-ol (2.18 mmol, 700 mg) was dissolved in 20 ml EtOH and hydrogenated overnight at 1 bar with Pd/C (10%) as catalyst. The catalyst was filtered and the solvent evaporated to give the desired product (635 mg, 100% yield) which was carried on to the next step without further purification. ES-MS: 292 (M+1). This reduction can be also accomplished using the following procedure: Na2S2O4 (140.0 mmol, 14 eq.) is dissolved in 150 mL water and 75 mL dioxane and 7.5 mL NH4OH solution are added. The corresponding nitro compound (10.0 mmol, 1 eq.) is added and the reaction mixture is stirred for 12 to 72 hours. Dioxane is evaporated and the product is extracted by using EtOAc or brine/THF. The organic phase is dried over MgSO4 and evaporated to give the desired product.

Workup

  1. filtrationThe catalyst was filtered
  2. customthe solvent evaporated

Sources & evidence

ORD record
ord-af9c0ffa8d024aba8afb40ea62c3d8e6
Source dataset
uspto-grants-2010_07
Patent number
US07759342B2

Reaction notes

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