Ethanol → HCID 178489570, compound

HRID 391660Notes

Reaction equation

HRID 391660 reaction equation
[NH2:1][C:2]1[C:3]([C:25](OCC)=[O:26])=[N:4][C:5]([NH:17][C@H:18]2[CH2:23][CH2:22][C@@H:21]([OH:24])[CH2:20][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].O[C@@H]1CC[C@H]([NH:37]C2N=C(C(OCC)=O)C([N+]([O-])=O)=C(NC3C=CC=CC=3OC)N=2)CC1.[CH2:61]([OH:63])C>[Pd]>[OH:24][C@@H:21]1[CH2:22][CH2:23][C@H:18]([NH:17][C:5]2[N:6]=[C:7]3[C:2]([NH:1][C:61](=[O:63])[N:8]3[C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=3[O:15][CH3:16])=[C:3]([C:25]([NH2:37])=[O:26])[N:4]=2)[CH2:19][CH2:20]1

Participants

5

Reactant 3

HCID 702EthanolHCID 178470293HCID 178470293, compoundHCID 178470295HCID 178470295, compound

Product 1

HCID 178489570HCID 178489570, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Ethyl 5-amino-2-(cis-4-hydroxycyclohexylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl 2-(cis-4-hydroxycyclohexylamino)-6-(2-methoxyphenyl-amino)-5-nitropyrimidine-4-carboxylate (0.340 g, 0.788 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.070 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 (0.272 g, 70%). MS (ESI) m/z 402.4 [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-6fc369a05a6044c0901b77d915366e32
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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