4-Amino-6-chloro-2-methylthiopyrimidine → tert-Butyl 1-[6-amino-2-(methylthio)pyrimidin-4-yl]piperidin-4-ylcarbamate

HRID 2233840Notes

Reaction equation

HRID 2233840 reaction equation
Cl[C:2]1[N:7]=[C:6]([S:8][CH3:9])[N:5]=[C:4]([NH2:10])[CH:3]=1.[NH:11]1[CH2:16][CH2:15][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:13][CH2:12]1>CN1C(=O)CCC1>[NH2:10][C:4]1[N:5]=[C:6]([S:8][CH3:9])[N:7]=[C:2]([N:11]2[CH2:12][CH2:13][CH:14]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:21])([CH3:23])[CH3:22])[CH2:15][CH2:16]2)[CH:3]=1

Participants

4

Reactant 2

HCID 704964-Amino-6-chloro-2-methylthiopyrimidineHCID 7238334-(N-Boc-amino)piperidine

Product 1

HCID 68580046tert-Butyl 1-[6-amino-2-(methylthio)pyrimidin-4-yl]piperidin-4-ylcarbamateYield 49.8%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

TEA (0.243 ml, 1.74 mmol) and 6-chloro-2-(methylthio)pyrimidin-4-amine (0.309 g, 1.74 mmol) were added to a solution of tert-butyl piperidin-4-ylcarbamate (0.35 g, 1.74 mmol) in NMP (4 ml). Using a Smith Microwave Synthesizer, the mixture was subjected to single-mode microwave at 150° C. for 90 minutes. The mixture was partitioned between water and EtOAc and washed (×2) with water. The organic phase was dried over magnesium sulphate and concentrated to give the title compound (0.294 g).

Workup

  1. customat 150° C.
  2. customfor 90 minutes
  3. customThe mixture was partitioned between water and EtOAc
  4. washwashed (×2) with water
  5. dry with materialThe organic phase was dried over magnesium sulphate
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-59fd88a441614460aee831a459a9a20f
Source dataset
uspto-grants-2010_05
Patent number
US07709503B2

Reaction notes

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