Triethylamine → HCID 67538830, compound

HRID 1192322Notes

Reaction equation

HRID 1192322 reaction equation
Cl[C:2]1[C:7]([I:8])=[CH:6][N:5]=[CH:4][N:3]=1.N1C=CC(=O)NC=1.CCN(CC)CC.[C:23]([N:30]1[CH2:35][CH2:34][NH:33][CH2:32][CH2:31]1)([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24]>CN1C(=O)CCC1>[C:26]([O:25][C:23]([N:30]1[CH2:35][CH2:34][N:33]([C:2]2[C:7]([I:8])=[CH:6][N:5]=[CH:4][N:3]=2)[CH2:32][CH2:31]1)=[O:24])([CH3:29])([CH3:27])[CH3:28]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 206954-HydroxypyrimidineHCID 143452tert-Butyl piperazine-1-carboxylateHCID 112302044-Chloro-5-iodopyrimidine

Product 1

HCID 67538830HCID 67538830, compoundYield 99%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 4-chloro-5-iodopyrimidine (3.00 g, 12.5 mmol) (prepared from 4(3H)-pyrimidinone according to the literature: Takao Sakamoto, et al. (1986) Chem. Pharm. Bull., 2719-2724), Et3N (5.22 mL, 37.4 mmol), 1-Boc piperazine (2.79 g, 15.0 mmol) and NMP (30 mL) was heated at 75° C. for 6 hours. After cooling, the reaction mixture was partitioned between EtOAc and water. The aqueous phase was extracted with EtOAc. The combined organic layers were washed with brine, dried and concentrated. The residue was purified by column chromatography (2:1 hexanes/EtOAc) to give 4-(5-Iodo-pyrimidin-4-yl)-piperazine-1-carboxylic acid tert-butyl ester (4.81 g, 99%) as a white solid. 1H NMR (CDCl3, 400 MHz) δ 8.70 (s, 1H), 8.62 (s, 1H), 3.57 (s, 8H), 1.49 (s, 9H). LCMS (APCI+) m/z 391 [M+H]+; Rt=2.96 minutes.

Workup

  1. temperatureAfter cooling
  2. customthe reaction mixture was partitioned between EtOAc and water
  3. extractionThe aqueous phase was extracted with EtOAc
  4. washThe combined organic layers were washed with brine
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by column chromatography (2:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-f363a1b07a09496dacc20acd759c1a16
Source dataset
uspto-grants-2014_03
Patent number
US08680114B2

Reaction notes

Loading…