Phosphorus oxychloride → HCID 86695329, compound

HRID 1182920Notes

Reaction equation

HRID 1182920 reaction equation
[NH2:1][C:2]1[N:7]=[C:6](O)[CH:5]=[C:4]([C:9]2([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=1.C(N(C(C)C)C(C)C)C.P(Cl)(Cl)([Cl:32])=O>C(#N)C>[Cl:32][C:6]1[CH:5]=[C:4]([C:9]2([C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][CH:15]=3)[CH2:13][CH2:12][CH2:11][CH2:10]2)[N:3]=[C:2]([NH2:1])[N:7]=1

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 81531DiisopropylethylamineHCID 178508960HCID 178508960, compound

Product 1

HCID 86695329HCID 86695329, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

360 mg of 2-amino-6-[1-(4-chlorophenyl)cyclopentyl]pyrimidin-4-ol are dissolved in 10 ml of acetonitrile, and 0.8 ml of N-ethyldiisopropylamine is added under nitrogen. 0.5 ml of phosphoryl chloride are subsequently added slowly. The batch is boiled under reflux for 8 h in order to complete the reaction. All volatile constituents are subsequently removed in vacuo, and the batch is added to ice-water and dichloromethane. The organic phase is dried over sodium sulfate, filtered and evaporated. The residue obtained is employed in the subsequent reaction without further purification. (Rt: 2.694 min.; M+H+: 308.2+310.2).

Workup

  1. temperatureunder reflux for 8 h in order
  2. customthe reaction
  3. customAll volatile constituents are subsequently removed in vacuo
  4. additionthe batch is added to ice-water and dichloromethane
  5. dry with materialThe organic phase is dried over sodium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe residue obtained
  9. customis employed in the subsequent reaction without further purification

Sources & evidence

ORD record
ord-89246f79d86d4a9fa63dcf5fc4551c5e
Source dataset
uspto-grants-2014_03
Patent number
US08664236B2

Reaction notes

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