Ethanol → HCID 24937107, compound

HRID 391651Notes

Reaction equation

HRID 391651 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-84165b666fc74b868a2a4571ab38003e
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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