Pyridine → 4-[2-Amino-6-(tetrahydro-furan-3-yl)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl ester

HRID 2075797Notes

Reaction equation

HRID 2075797 reaction equation
Cl[C:2]1[CH:7]=[C:6]([CH:8]2[CH2:12][CH2:11][O:10][CH2:9]2)[N:5]=[C:4]([NH2:13])[N:3]=1.[C:14]([N:21]1[CH2:26][CH2:25][NH:24][CH2:23][CH2:22]1)([O:16][C:17]([CH3:20])([CH3:19])[CH3:18])=[O:15].N1C=CC=CC=1>CCO>[C:17]([O:16][C:14]([N:21]1[CH2:26][CH2:25][N:24]([C:2]2[CH:7]=[C:6]([CH:8]3[CH2:12][CH2:11][O:10][CH2:9]3)[N:5]=[C:4]([NH2:13])[N:3]=2)[CH2:23][CH2:22]1)=[O:15])([CH3:20])([CH3:18])[CH3:19]

Participants

5

Reactant 3

HCID 1049PyridineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 866223774-Chloro-6-(tetrahydro-furan-3-yl)-pyrimidin-2-ylamine

Product 1

HCID 670962764-[2-Amino-6-(tetrahydro-furan-3-yl)-pyrimidin-4-yl]-piperazine-1-carboxylic acid tert-butyl esterYield 14.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 4-chloro-6-(tetrahydro-furan-3-yl)-pyrimidin-2-ylamine (500 mg, 2.51 mmol), N-BOC piperazine (960 mg, 5.15 mmol) and pyridine (500 uL, 6.1 mmol) in EtOH (10 mL) was heated at 90° C. for 4 h. Upon cooling to rt a thick precipitate formed which was collected by filtration. The material was rinsed with EtOAc to afford 125 mg of a white solid. The filtrate was concentrated and triturated with Et2O-EtOAc (1:1) to yield an additional 600 mg of material (82% combined). MS (ESI): mass calcd. for C17H27N5O3, 349.2; m/z found, 350.3 [M+H]+. 1H NMR (CDCl3): 5.86 (s, 1H), 4.70 (br s, 2H), 3.90-4.07 (m, 2H), 3.83-3.90 (m, 2H), 3.55-3.60 (m, 4H), 3.45-3.50 (m, 4H), 3.18-3.26 (m, 1H), 2.20-2.30 (m, 1H), 2.09-2.18 (m, 1H), 1.48 (s, 9H).

Workup

  1. customformed which
  2. filtrationwas collected by filtration
  3. washThe material was rinsed with EtOAc

Sources & evidence

ORD record
ord-c7cecb6254a24c9498d28e69bacddf22
Source dataset
uspto-grants-2011_04
Patent number
US07923451B2

Reaction notes

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