Tert-butyl {6-[3-(2-methyl-5-nitro-phenyl)-1-methyl-ureido]-pyrimidin-4-yl}-carbamate → tert-Butyl {6-[3-(5-Amino-2-methyl-Phenyl)-1-methyl-ureido]-pyrimidin-4-yl}-carbamate

HRID 1038732Notes

Reaction equation

HRID 1038732 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-])=O)=[CH:4][C:3]=1[NH:11][C:12](=[O:29])[N:13]([C:15]1[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:27])([CH3:26])[CH3:25])[CH:16]=1)[CH3:14]>CO.CN(C=O)C.[Pd]>[NH2:8][C:5]1[CH:6]=[CH:7][C:2]([CH3:1])=[C:3]([NH:11][C:12](=[O:29])[N:13]([C:15]2[N:20]=[CH:19][N:18]=[C:17]([NH:21][C:22](=[O:28])[O:23][C:24]([CH3:25])([CH3:26])[CH3:27])[CH:16]=2)[CH3:14])[CH:4]=1

Participants

5

Reactant 1

HCID 86630719Tert-butyl {6-[3-(2-methyl-5-nitro-phenyl)-1-methyl-ureido]-pyrimidin-4-yl}-carbamate

Product 1

HCID 86630718tert-Butyl {6-[3-(5-Amino-2-methyl-Phenyl)-1-methyl-ureido]-pyrimidin-4-yl}-carbamate

Reagents, catalysts & solvents 3

HCID 23938PalladiumCatalystHCID 887MethanolSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of tert-butyl {6-[3-(2-methyl-5-nitro-phenyl)-1-methyl-ureido]-pyrimidin-4-yl}-carbamate (330 mg, 0.82 mmol) in a mixture of methanol (20 ml) and DMF (50 ml) is hydrogenated in the presence of 10% palladium on charcoal (500 mg) at atmospheric pressure. After 20 h the hydrogenation is complete and the catalyst is filtered off. The filtrate is evaporated to dryness. The residue obtained is triturated with ether, filtered off, and vacuum dried to afford a gray powder: HPLC: tR=5.38 min (purity: 97%, gradient A), ESI-MS: 373.4 [MH]+.

Workup

  1. filtrationthe catalyst is filtered off
  2. customThe filtrate is evaporated to dryness
  3. customThe residue obtained
  4. customis triturated with ether
  5. filtrationfiltered off
  6. customvacuum dried
  7. customto afford a gray powder

Sources & evidence

ORD record
ord-96aaa287cc554197b10fc9f6f7acebae
Source dataset
uspto-grants-2013_10
Patent number
US08552002B2

Reaction notes

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