Phosphorus oxychloride → 4-Chloro-6-(4-phenoxyphenyl)-2-phenylpyrimidine-5-carbonitrile

HRID 81042Notes

Reaction equation

HRID 81042 reaction equation
O=[C:2]1[NH:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)=[C:3]1[C:27]#[N:28].P(Cl)(Cl)([Cl:31])=O>>[Cl:31][C:2]1[C:3]([C:27]#[N:28])=[C:4]([C:14]2[CH:19]=[CH:18][C:17]([O:20][C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)=[CH:16][CH:15]=2)[N:5]=[C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:7]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 1363723496-Oxo-4-(4-phenoxyphenyl)-2-phenyl-1,6-dihydropyrimidine-5-carbonitrile

Product 1

HCID 866656894-Chloro-6-(4-phenoxyphenyl)-2-phenylpyrimidine-5-carbonitrile

Conditions

Temperature
90 °C

Procedure

A mixture of crude 6-oxo-4-(4-phenoxyphenyl)-2-phenyl-1,6-dihydropyrimidine-5-carbonitrile and phosphorus oxychloride (4 mL) was stirred at 90° C. for 1 h, concentrated, dissolved in dichloromethane (10 mL) and water (20 mL) and carefully neutralized with solid potassium carbonate until CO2 bubbling stopped. The mixture was extracted with dichloromethane (3×5 mL). The combined extracts were dried (MgSO4) and concentrated to give crude 4-chloro-6-(4-phenoxyphenyl)-2-phenylpyrimidine-5-carbonitrile as tan solid. The crude material was taken to next reaction without purification. MS (ES+) m/z: 384 (M+H); LC retention time: 5.190 min (analytical HPLC Method 13 except with 2 min hold at 100% B).

Workup

  1. concentrationconcentrated
  2. dissolutiondissolved in dichloromethane (10 mL)
  3. extractionThe mixture was extracted with dichloromethane (3×5 mL)
  4. dry with materialThe combined extracts were dried (MgSO4)
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-cb2f127676db46c6adbc727d334b65f6
Source dataset
uspto-grants-2014_09
Patent number
US08846673B2

Reaction notes

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