Ethanol → HCID 178489571, compound

HRID 391657Notes

Reaction equation

HRID 391657 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 178470294HCID 178470294, compoundHCID 178470296HCID 178470296, compound

Product 1

HCID 178489571HCID 178489571, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 23938PalladiumCatalyst

Procedure

Ethyl 5-amino-2-(trans-4-hydroxycyclohexylamino)-6-(2-methoxyphenylamino)pyrimidine-4-carboxylate. Ethyl 2-(trans-4-hydroxycyclohexylamino)-6-(2-methoxyphenyl-amino)-5-nitropyrimidine-4-carboxylate (0.300 g, 0.852 mmol) was dissolved in ethanol (20 mL) and 10% palladium on carbon (0.073 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 (5% methanol in ethyl acetate) to afford the title compound (0.240 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-eb8bfcecf81342098bd9e05a301c07a8
Source dataset
uspto-grants-2013_02
Patent number
US08383634B2

Reaction notes

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