Acetonitrile → [2-Methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl]-(4-trifluoromethyl-phenyl)-amine

HRID 1186118Notes

Reaction equation

HRID 1186118 reaction equation
Cl[C:2]1[C:12]2[CH2:11][CH2:10][N:9]([C:13]3[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:8][CH2:7][C:6]=2[N:5]=[C:4]([S:23][CH3:24])[N:3]=1.CSC1N=C(O)C2CCN([C:37]3[C:42]([C:43]([F:46])([F:45])[F:44])=[CH:41][CH:40]=[CH:39][N:38]=3)CCC=2N=1.O=P(Cl)(Cl)Cl.[CH3:54]C#N>CCOC(C)=O>[CH3:24][S:23][C:4]1[N:3]=[C:2]([NH:38][C:39]2[CH:40]=[CH:41][C:42]([C:43]([F:44])([F:45])[F:46])=[CH:37][CH:54]=2)[C:12]2[CH2:11][CH2:10][N:9]([C:13]3[C:18]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:16]=[CH:15][N:14]=3)[CH2:8][CH2:7][C:6]=2[N:5]=1

Participants

6

Reactant 4

HCID 6342AcetonitrileHCID 24813Phosphorus oxychlorideHCID 866153084-Chloro-2-methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepineHCID 178503519HCID 178503519, compound

Product 1

HCID 58972614[2-Methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-yl]-(4-trifluoromethyl-phenyl)-amineYield 89%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

4-Chloro-2-methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepine. To a solution of 2-methylsulfanyl-7-(3-trifluoromethyl-pyridin-2-yl)-6,7,8,9-tetrahydro-5H-pyrimido[4,5-d]azepin-4-ol (1.8 g, 4.92 mmol) in CH3CN (40 mL) was added POCl3 (1.4 mL, 14.8 mmol). After 15 min at 80° C., the mixture was cooled to rt, diluted with EtOAc, and quenched slowly with satd. aq. NaHCO3. The organic layer was separated, dried (MgSO4), and concentrated. The crude residue was purified (FCC) to give the title compound (1.6 g, 89%).

Workup

  1. customquenched slowly with satd
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated
  5. customThe crude residue was purified (FCC)

Sources & evidence

ORD record
ord-a1bdc3f1a23a4c42aef9f02dbe1ff387
Source dataset
uspto-grants-2014_03
Patent number
US08673895B2

Reaction notes

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