Triethylamine → HCID 69026638, compound

HRID 217898Notes

Reaction equation

HRID 217898 reaction equation
[NH2:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]2[C:9](=[O:19])[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][N:14]=3)[N:12]=[C:3]12.C(N(CC)CC)C.Cl[C:28]([O:30][CH2:31][CH3:32])=[O:29]>O1CCCC1>[CH2:31]([O:30][C:28](=[O:29])[NH:1][CH:2]1[CH2:8][CH2:7][CH2:6][CH2:5][N:4]2[C:9](=[O:19])[CH:10]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][N:14]=3)[N:12]=[C:3]12)[CH3:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10928Ethyl chloroformateHCID 67265735HCID 67265735, compound2×

Product 1

HCID 69026638HCID 69026638, compoundYield 72.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.3 g (1.17 mmol) of (+/−)10-amino-2-pyrimidin-4-yl-7,8,9,10-tetrahydropyrimido[1,2-a]azepin-4(6H)-one (compound 3.4 of example 3) was diluted in 8 mL of tetrahydrofuran. 0.18 mL (1.28 mmol) of triethylamine was added at 0° C. and the mixture was stirred for 10 min and 0.12 mL (1.28 mmol) of ethyl chloroformate was added. The resulting mixture was stirred at room temperature for 1 h and quenched by adding a saturated solution of ammonium chloride. The product was extracted with dichloromethane, dried over sodium sulfate and the solvent was evaporated. The residue was triturated with diethyl ether and filtered to afford 0.28 g (72%) of (4-oxo-2-pyrimidin-4-yl-4,6,7,8,9,10-hexahydro-pyrimido[1,2-a]azepin-10-yl)-carbamic acid ethyl ester as a yellow solid (Mp.: 168-170° C.). The compound was used as such in the next step.

Workup

  1. stirringThe resulting mixture was stirred at room temperature for 1 h
  2. customquenched
  3. additionby adding a saturated solution of ammonium chloride
  4. extractionThe product was extracted with dichloromethane
  5. dry with materialdried over sodium sulfate
  6. customthe solvent was evaporated
  7. customThe residue was triturated with diethyl ether
  8. filtrationfiltered

Sources & evidence

ORD record
ord-bb5910cc3d44437194afbf40720aab64
Source dataset
uspto-grants-2012_06
Patent number
US08198287B2

Reaction notes

Loading…