Phosphorus oxychloride → HCID 86665890, compound

HRID 75429Notes

Reaction equation

HRID 75429 reaction equation
[CH:1]12[O:8][CH:5]([CH2:6][CH2:7]1)[CH2:4][N:3]([C:9]1[CH:14]=[C:13]([O:15][CH:16]([CH3:18])[CH3:17])[N:12]=[C:11](O)[N:10]=1)[CH2:2]2.O=P(Cl)(Cl)[Cl:22]>>[Cl:22][C:11]1[N:10]=[C:9]([N:3]2[CH2:4][CH:5]3[O:8][CH:1]([CH2:7][CH2:6]3)[CH2:2]2)[CH:14]=[C:13]([O:15][CH:16]([CH3:18])[CH3:17])[N:12]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178458588HCID 178458588, compound

Product 1

HCID 86665890HCID 86665890, compoundYield 46%

Conditions

Temperature
100 °C

Procedure

In a 25 mL round-bottomed flask was placed 4-(8-oxa-3-azabicyclo[3.2.1]octan-3-yl)-6-isopropoxypyrimidin-2-ol (31, 215 mg, 0.810 mmol) in POCl3 (20 ml) to give a fine off-white suspension. The mixture was stirred at 100° C. for 16 h. The mixture was cooled to room temperature, concentrated, diluted with dichloromethane, and washed with saturated NaHCO3. The aqueous phase was made basic with NaOH (5N) to pH 10 and extracted with dichloromethane. The combined organic phases were dried over MgSO4, filtered and concentrated to give the title compound (106 mg, 46%). Aryl chloride 32 could be transformed into aniline 19 as described in scheme 2 for the conversion of 5 into 6. Aniline 19 could be transformed into urea or carbamate compounds as described in scheme 2 (and illustrated in the experimental section for scheme 8).

Workup

  1. customIn a 25 mL round-bottomed flask was placed
  2. temperatureThe mixture was cooled to room temperature
  3. concentrationconcentrated
  4. additiondiluted with dichloromethane
  5. washwashed with saturated NaHCO3
  6. extractionextracted with dichloromethane
  7. dry with materialThe combined organic phases were dried over MgSO4
  8. filtrationfiltered
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-52cf58d9b0d345ae9e0cdc30e0fb0568
Source dataset
uspto-grants-2014_09
Patent number
US08835429B2

Reaction notes

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