Ethanol → (R)-9-(2-Methoxyphenyl)-8-oxo-2-(pyrrolidin-3-ylamino)-8,9-dihydro-7H-purine-6-carboxamide

HRID 2427983Notes

Reaction equation

HRID 2427983 reaction equation
[NH2:1][C:2]1[C:3]([C:30]([O:32]CC)=O)=[N:4][C:5]([NH:17][C@@H:18]2[CH2:22][CH2:21][N:20](C(OC(C)(C)C)=O)[CH2:19]2)=[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:42]1CC[C@@H](NC2N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC3C=CC=CC=3OC)N=2)C1)=O)(C)(C)C.[CH2:71]([OH:73])C>[Pd]>[CH3:16][O:15][C:10]1[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=1[N:8]1[C:71](=[O:73])[NH:1][C:2]2[C:7]1=[N:6][C:5]([NH:17][C@@H:18]1[CH2:22][CH2:21][NH:20][CH2:19]1)=[N:4][C:3]=2[C:30]([NH2:42])=[O:32]

Participants

5

Reactant 3

HCID 702EthanolHCID 86627704(R)-Ethyl 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylateHCID 86627705(R)-Ethyl 5-amino-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxy-phenylamino)pyrimidine-4-carboxylate

Product 1

HCID 24937106(R)-9-(2-Methoxyphenyl)-8-oxo-2-(pyrrolidin-3-ylamino)-8,9-dihydro-7H-purine-6-carboxamideYield 89%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

(R)-Ethyl 5-amino-2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxy-phenylamino)pyrimidine-4-carboxylate. (R)-Ethyl 2-(1-(tert-butoxycarbonyl)pyrrolidin-3-ylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate (0.403 g, 0.802 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.080 g) were added to the flask and flushed with fresh hydrogen gas and allowed to stir at room temperature. After 16 hours, 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, 89%). 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-85299183c7714f2fa5500908dc0755b0
Source dataset
uspto-grants-2011_06
Patent number
US07968556B2

Reaction notes

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