Methanol → HCID 178438985, compound

HRID 1005797Notes

Reaction equation

HRID 1005797 reaction equation
C([O:3][C:4](=O)[CH2:5][C:6]([C:8]1[CH:13]=[CH:12][C:11]([S:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[CH:21]([CH3:23])[CH3:22])=[C:10]([C:24]([F:27])([F:26])[F:25])[CH:9]=1)=O)C.Cl.[CH:30]([NH2:32])=[NH:31].CO>CC(O)=O.CN(C=O)C>[CH:21]([C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=1[S:14][C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:32]=[CH:30][N:31]=[C:4]([OH:3])[CH:5]=2)=[CH:9][C:10]=1[C:24]([F:27])([F:26])[F:25])([CH3:23])[CH3:22]

Participants

6

Reactant 3

HCID 887MethanolHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 60108854HCID 60108854, compound

Product 1

HCID 178438985HCID 178438985, compoundYield 14%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

Then, 6-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyrmidin-4-ol 46 was prepared as follows. The mixture of compound 45 (10.6 g, 25.8 mmol) and formamidine hydrochloride (10.4 g, 129 mmol) in 20% HOAc in DMF (50 mL) was heated at 120° C. for 3 days. MeOH (50 mL) was added and the resulting solution was purified on a preparative HPLC column, C8 reverse-phase column, eluted with NH4OAc-H2O—CH3CN. Evaporation of solvents gave a white solid 46 (1.40 g, 14%); MS (APCI) m/z 391 (M+H)+.

Workup

  1. customThen, 6-(4-(2-isopropyl-phenylsulfanyl)-3-trifluoromethyl-phenyl)-pyrmidin-4-ol 46 was prepared
  2. customthe resulting solution was purified on a preparative HPLC column, C8 reverse-phase column
  3. washeluted with NH4OAc-H2O—CH3CN
  4. customEvaporation of solvents

Sources & evidence

ORD record
ord-1c6a20b0179842c7945e6bb6e1711978
Source dataset
uspto-grants-2004_09
Patent number
US06787542B2

Reaction notes

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