Triethylamine → HCID 136383531, compound

HRID 1985738Notes

Reaction equation

HRID 1985738 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[N:8]=[C:9]3[NH:18][C:13]4([CH2:17][CH2:16][NH:15][CH2:14]4)[CH2:12][CH2:11][N:10]3[C:19](=[O:21])[CH:20]=2)=[N:3][CH:2]=1.C(N(CC)CC)C.[F:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33](Cl)=[O:34].[Cl-].[NH4+]>O1CCCC1>[F:29][C:30]1[CH:31]=[C:32]([CH:36]=[CH:37][CH:38]=1)[C:33]([N:15]1[CH2:16][CH2:17][C:13]2([CH2:12][CH2:11][N:10]3[C:19](=[O:21])[CH:20]=[C:7]([C:4]4[CH:5]=[CH:6][N:1]=[CH:2][N:3]=4)[N:8]=[C:9]3[NH:18]2)[CH2:14]1)=[O:34]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 25517Ammonium ChlorideHCID 743763-Fluorobenzoyl chlorideHCID 136346459HCID 136346459, compound

Product 1

HCID 136383531HCID 136383531, compoundYield 72.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 0.3 g (1.055 mmol) of 8-pyrimidin-4-yl-3,4-dihydrospiro [pyrimido[1,2-a]pyrimidine-2,3′-pyrrolidin]-6(1H)-one dissolved in 5 ml of tetrahydrofuran at room temperature were added 0.18 ml (1.27 mmol) of triethylamine and 0.152 ml (1.27 mmol) of 3-fluoro-benzoyl chloride. The resulting mixture was stirred at room temperature under nitrogen atmosphere for 2h. The reaction mixture was added to a saturated aqueous solution of ammonium chloride, extracted with a mixture of dichloromethane/menthanol in the proportions of 100/0 to 80/20, dried and evaporated. The residue was purified by chromatography on silica gel eluting with a mixture of dichloromethane/menthanol in the proportions of 100/0 to 70/30 to give 0.310 g (72%) of pure product as grey solid. Mp: 296-298° C.

Workup

  1. extractionextracted with a mixture of dichloromethane/menthanol in the proportions of 100/0 to 80/20
  2. customdried
  3. customevaporated
  4. customThe residue was purified by chromatography on silica gel eluting with a mixture of dichloromethane/menthanol in the proportions of 100/0 to 70/30

Sources & evidence

ORD record
ord-4be344ffe44e4ac58d314742b1312e78
Source dataset
uspto-grants-2009_06
Patent number
US07547705B2

Reaction notes

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