Ethanol → HCID 24937107, compound

HRID 2427986Notes

Reaction equation

HRID 2427986 reaction equation
C(O[C:4]([C:6]1[C:11]([N+:12]([O-])=O)=[C:10]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[O:22][CH3:23])[N:9]=[C:8]([NH:24][C@H:25]2[CH2:29][CH2:28][N:27](C(OC(C)(C)C)=O)[CH2:26]2)[N:7]=1)=[O:5])C.[NH2:37]C1C(C(OCC)=O)=NC(N[C@H]2CCN(C(OC(C)(C)C)=O)C2)=NC=1NC1C=CC=CC=1OC.[CH2:71]([OH:73])C>[Pd]>[CH3:23][O:22][C:17]1[CH:18]=[CH:19][CH:20]=[CH:21][C:16]=1[N:15]1[C:71](=[O:73])[NH:12][C:11]2[C:10]1=[N:9][C:8]([NH:24][C@H:25]1[CH2:29][CH2:28][NH:27][CH2:26]1)=[N:7][C:6]=2[C:4]([NH2:37])=[O:5]

Participants

4

Reactant 2

HCID 702EthanolHCID 86627710HCID 86627710, compound

Product 1

HCID 24937107HCID 24937107, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(S)-Ethyl 5-amino-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxy-phenylamino)pyrimidine-4-carboxylate (S)-Ethyl 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (0.424 g, 0.844 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.085 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 (0.357 g, 94%). MS (ESI) m/z 473.5 [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-8e67d667033144efbb7d129c9e280dbc
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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