Water → HCID 117678104, compound

HRID 1778169Notes

Reaction equation

HRID 1778169 reaction equation
Cl[C:2]1[CH:7]=[C:6]([Cl:8])[N:5]=[C:4]([S:9][CH3:10])[N:3]=1.CCN(C(C)C)C(C)C.[CH:20]12[CH2:26][CH:23]([NH:24][CH2:25]1)[CH2:22][O:21]2.O>CN(C=O)C>[Cl:8][C:6]1[N:5]=[C:4]([S:9][CH3:10])[N:3]=[C:2]([N:24]2[CH2:25][C@@H:20]3[CH2:26][C@H:23]2[CH2:22][O:21]3)[CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 805314,6-Dichloro-2-(methylthio)pyrimidineHCID 81531DiisopropylethylamineHCID 36145512-Oxa-5-azabicyclo(2.2.1)heptane

Product 1

HCID 117678104HCID 117678104, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
50 °C

Procedure

The mixture of 4,6-dichloro-2-(methylthio)pyrimidine (450 mg, 2.31 mmol), DIEA (894 mg, 6.92 mmol) and 2-oxa-5-azabicyclo[2.2.1]heptane (328 mg, 2.42 mmol) in DMF (5 mL) was stirred at 50° C. for 12 h. Water (20 mL) was added to and extracted with ethyl acetate (2×20 mL). The organic layers were dried over Na2SO4, filtered and concentrated to give (1S,4S)-5-(6-chloro-2-(methylthio)pyrimidin-4-yl)-2-oxa-5-azabicyclo-[2.2.1]heptane (550 mg, 92.5% yield) as a white solid, which was used for next step without further purification LCMS (ESI): [MH]+=258.0.

Workup

  1. extractionextracted with ethyl acetate (2×20 mL)
  2. dry with materialThe organic layers were dried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-ed1ed4327a254fbd99e2dbc58158eb70
Source dataset
uspto-grants-2016_02
Patent number
US09266862B2

Reaction notes

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