Phosphorus oxychloride → HCID 86695329, compound

HRID 591215Notes

Reaction equation

HRID 591215 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-f93d2e90ca544dcb95b274b38fa48d21
Source dataset
uspto-grants-2016_01
Patent number
US09238651B2

Reaction notes

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