Ethanol → HCID 57474695, compound

HRID 391673Notes

Reaction equation

HRID 391673 reaction equation
[NH2:1][C:2]1[C:3]([C:21]([O:23]CC)=O)=[N:4][C:5]([NH:17][CH2:18][CH2:19][OH:20])=[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].OCC[NH:29]C1N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC2C=CC=CC=2OC)N=1.[CH2:53]([OH:55])C>[Pd]>[OH:20][CH2:19][CH2:18][NH:17][C:5]1[N:6]=[C:7]2[C:2]([NH:1][C:53](=[O:55])[N:8]2[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:15][CH3:16])=[C:3]([C:21]([NH2:29])=[O:23])[N:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 86627723HCID 86627723, compoundHCID 86627724HCID 86627724, compound

Product 1

HCID 57474695HCID 57474695, compoundYield 87%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Ethyl 5-amino-2-(2-hydroxyethylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl 2-(2-hydroxyethylamino)-6-(2-methoxyphenylamino)-5-nitropyrimidine-4-carboxylate r. (0.250 g, 0.663 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.050 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 (5% methanol in ethyl acetate) to afford the title compound (0.200 g, 87%). MS (ESI) m/z 348.1 [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-5e7814964003410db3eb083443fd36bb
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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