Methyl 2-(3-(tert-butoxycarbonylamino)prop-1-ynyl)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate → Methyl 2-(3-(tert-butoxycarbonylamino)propyl)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

HRID 2092799Notes

Reaction equation

HRID 2092799 reaction equation
[C:1]([O:5][C:6]([NH:8][CH2:9][C:10]#[C:11][C:12]1[N:17]=[C:16]([CH3:18])[C:15]([C:19]([O:21][CH3:22])=[O:20])=[C:14]([NH:23][C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)[N:13]=1)=[O:7])([CH3:4])([CH3:3])[CH3:2]>CCO.[Pd]>[C:1]([O:5][C:6]([NH:8][CH2:9][CH2:10][CH2:11][C:12]1[N:17]=[C:16]([CH3:18])[C:15]([C:19]([O:21][CH3:22])=[O:20])=[C:14]([NH:23][C:24]2[CH:25]=[C:26]([CH3:30])[CH:27]=[CH:28][CH:29]=2)[N:13]=1)=[O:7])([CH3:3])([CH3:4])[CH3:2]

Participants

4

Reactant 1

HCID 58317513Methyl 2-(3-(tert-butoxycarbonylamino)prop-1-ynyl)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

Product 1

HCID 58317633Methyl 2-(3-(tert-butoxycarbonylamino)propyl)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

Methyl 2-(3-(tert-butoxycarbonylamino)prop-1-ynyl)-4-methyl-6-(m-tolylamino)pyrimidine-5-carboxylate (0.190 g, 0.463 mmol) was dissolved in EtOH (4 mL). To this solution was added palladium on carbon (0.049 g, 0.046 mmol) and the resulting mixture was stirred overnight at RT under H2 atmosphere. The mixture was filtered through a pad of Celite, and the filtrate was evaporated to give the title compound as a brown oil, which was used in next step without further purification. [M+H] calc'd for C22H30N4O4, 415. found, 415.

Workup

  1. filtrationThe mixture was filtered through a pad of Celite
  2. customthe filtrate was evaporated

Sources & evidence

ORD record
ord-423ffa092bb94c37ba18d57df03d0e30
Source dataset
uspto-grants-2013_05
Patent number
US08440689B2

Reaction notes

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