4-Amino-2,2,6,6-tetramethylpiperidine → HCID 178426364, compound

HRID 1434912Notes

Reaction equation

HRID 1434912 reaction equation
CS[C:3]1[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][N:4]=1.[CH3:10][C:11]1([CH3:20])[CH2:16][CH:15]([NH2:17])[CH2:14][C:13]([CH3:19])([CH3:18])[NH:12]1>>[CH3:10][C:11]1([CH3:20])[CH2:16][CH:15]([NH:17][C:3]2[N:8]=[C:7]([OH:9])[CH:6]=[CH:5][N:4]=2)[CH2:14][C:13]([CH3:19])([CH3:18])[NH:12]1

Participants

3

Reactant 2

HCID 375244-Amino-2,2,6,6-tetramethylpiperidineHCID 178503462HCID 178503462, compound

Product 1

HCID 178426364HCID 178426364, compoundYield 93.1%

Procedure

Neat 2-methylsulfanyl-pyrimidin-4-ol (5 g, 35 mmol) and 2,2,6,6-tetramethyl-piperidin-4-ylamine (8.243 g, 52.75 mmol) were heated to 170° C. with stirring for 2 hours. After cooling, the brown solid was triturated with ether. Filtration gave 8.16 g (93%) of 2-(2,2,6,6-Tetramethyl-piperidin-4-ylamino)-pyrimidin-4-ol. This crude (8 g, 32 mmol) was suspended in 160 ml of acetonitrile. Then, 4N-HCl in dioxane (24 ml, 96 mmol) and POCl3 (7.32 ml, 80 mmol) were added successively and the suspension was heated to reflux (105° C. heat bath) for 2 hours. After that, the mixture was cooled, diluted with EtOAc and washed twice with 2N-NaOH, then brine, dried over sodium sulfate and evaporated. Chromatography on silicagel (EtOAc/MeOH/ammonia:2/1/0.02) gave (4-chloro-pyrimidin-2-yl)-(2,2,6,6-tetramethyl-piperidin-4-yl)-amine as a beige solid. Yield: 7.68 g (89%).

Workup

  1. temperatureAfter cooling
  2. customthe brown solid was triturated with ether
  3. filtrationFiltration

Sources & evidence

ORD record
ord-9bc3080251bf4a25991e70d76825c95c
Source dataset
uspto-grants-2009_11
Patent number
US07615562B2

Reaction notes

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