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 516034Notes

Reaction equation

HRID 516034 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-453e700257b54a8dbac20edddd75b492
Source dataset
uspto-grants-2015_08
Patent number
US09108970B2

Reaction notes

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