Ethanol → HCID 66647723, compound

HRID 2428004Notes

Reaction equation

HRID 2428004 reaction equation
[NH2:1][C:2]1[C:3]([C:31]([O:33]CC)=O)=[N:4][C:5]([NH:17][CH2:18][C@@H:19]2[CH2:23][CH2:22][CH2:21][N:20]2C(OC(C)(C)C)=O)=[N:6][C:7]=1[NH:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[O:15][CH3:16].C(OC([N:43]1CCC[C@H]1CNC1N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=1)=O)(C)(C)C.[CH2:73]([OH:75])C>[Pd]>[CH3:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:8]1[C:73](=[O:75])[NH:1][C:2]2[C:7]1=[N:6][C:5]([NH:17][CH2:18][C@@H:19]1[CH2:23][CH2:22][CH2:21][NH:20]1)=[N:4][C:3]=2[C:31]([NH2:43])=[O:33]

Participants

5

Reactant 3

HCID 702EthanolHCID 86627719HCID 86627719, compoundHCID 86627720HCID 86627720, compound

Product 1

HCID 66647723HCID 66647723, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(S)-Ethyl 5-amino-2-((1-(tert-butoxycarbonyl)pyrrolidin-2-yl)methylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. (S)-Ethyl 2-((1-(tert-butoxycarbonyl)pyrrolidin-2-yl)methylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (0.416 g, 0.802 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.083 g) were added to the flask and flushed with fresh hydrogen gas and allowed to stir at room temperature. After 16 h, the reaction was filtered through celite and the filtrate condensed under reduced pressure. The crude oil was purified using Biotage chromatography (0-100% ethyl acetate in hexanes) to afford the title compound (0.340 g, 84%). MS (ESI) m/z 487.6 [M+1]+.

Workup

  1. customflushed with fresh hydrogen gas
  2. filtrationthe reaction was filtered through celite
  3. customthe filtrate condensed under reduced pressure
  4. customThe crude oil was purified

Sources & evidence

ORD record
ord-d0bba6b71ac74513b1364403fa85e697
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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