Sodium → 7-benzyl-4-phenyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine

HRID 239114Notes

Reaction equation

HRID 239114 reaction equation
[Na].Cl.[CH:3]([NH2:5])=[NH:4].[CH2:6]([N:13]1[CH2:19][CH2:18][C:17](Cl)=[C:16]([C:21]([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)=O)[CH2:15][CH2:14]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1>C(O)C>[CH2:6]([N:13]1[CH2:14][CH2:15][C:16]2[C:21]([C:23]3[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=3)=[N:4][CH:3]=[N:5][C:17]=2[CH2:18][CH2:19]1)[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

5

Reactant 3

HCID 5360545SodiumHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 69190815(1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepin-4-yl)-phenyl-methanone

Product 1

HCID 866860407-benzyl-4-phenyl-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepineYield 39.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
6 °C

Procedure

16.8 g sodium was added to 500 mL ethanol at 10° C. Then, 48.5 g formamidine hydrochloride was added and the reaction was stirred 15 min at 6° C. 28 g (1-benzyl-5-chloro-2,3,6,7-tetrahydro-1H-azepin-4-yl)-phenyl-methanone was added and the reaction was stirred 17 h at RT and 1 h at 40° C. The mixture was filtered and the solvent was removed. The residue was dissolved in ethyl acetate. The layers were separated and the organic layer was washed with water and evaporated. The residue was crystallized with diethylether to yield 10.7 g of the desired product. Fp: 81-82° C.

Workup

  1. stirringthe reaction was stirred 17 h at RT and 1 h at 40° C
  2. filtrationThe mixture was filtered
  3. customthe solvent was removed
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. customThe layers were separated
  6. washthe organic layer was washed with water
  7. customevaporated
  8. customThe residue was crystallized with diethylether

Sources & evidence

ORD record
ord-5080a0aef6f745e6b0f5a947c25647a3
Source dataset
uspto-grants-2014_02
Patent number
US08642774B2

Reaction notes

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