Water → 2-amino-8-phenyl-1,5,6,7,8,9-hexahydrocyclohepta[d]pyrimidin-4-one

HRID 2386997Notes

Reaction equation

HRID 2386997 reaction equation
O=[C:2]1[CH2:8][CH:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)[CH2:6][CH2:5][CH2:4][CH:3]1[C:15]([O:17]C)=O.[N+]([O-])(O)=O.[NH2:23][C:24]([NH2:26])=[NH:25].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O.C(O)(=O)C>[NH2:26][C:24]1[N:23]=[C:15]([OH:17])[C:3]2[CH2:4][CH2:5][CH2:6][CH:7]([C:9]3[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=3)[CH2:8][C:2]=2[N:25]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10481Guanidine NitrateHCID 11430Potassium CarbonateHCID 68603292HCID 68603292, compound

Product 1

HCID 1785088762-amino-8-phenyl-1,5,6,7,8,9-hexahydrocyclohepta[d]pyrimidin-4-one

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of Example 11A (1.86 g, 7.55 mmol), guanidine nitrate (1.84 g, 15.1 mmol), and potassium carbonate (2.09 g, 15.1 mmol) was heated in N,N-dimethylformamide (7.5 mL) at 120° C. overnight. After this time, the mixture was cooled to room temperature and poured into water. The liquid was adjusted to pH 5 with acetic acid, then the precipitate was collected by filtration, washed with water, and air-dried. It was further dried by azeotroping with toluene to yield the title compound. 1H NMR (300 MHz, DMSO-d6) δ 10.73 (m, 1H), 7.26 (m, 5H), 6.26 (s, 2H), 3.10 (s, 1H), 3.00 (dd, J=14.67, 6.35 Hz, 1H), 2.60 (t, J=13.68 Hz, 1H), 2.39 (d, J=13.48 Hz, 1H), 2.10 (m, 1H), 1.88 (m, 3H), 1.22 (m, 1H); MS (DCI+) m/z 256 (M+H)+.

Workup

  1. filtrationthe precipitate was collected by filtration
  2. washwashed with water
  3. customair-dried
  4. customIt was further dried
  5. customby azeotroping with toluene

Sources & evidence

ORD record
ord-342bd7e4390c4929940b26724c98f78e
Source dataset
uspto-grants-2012_09
Patent number
US08268846B2

Reaction notes

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