Ammonium Hydroxide → HCID 58199536, compound

HRID 452391Notes

Reaction equation

HRID 452391 reaction equation
[N:1]1[C:6]2[CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][C:5]=2[C:4](O)=[N:3][CH:2]=1.O=P(Cl)(Cl)[Cl:16].[OH-].[NH4+]>>[Cl:16][C:4]1[C:5]2[CH2:12][CH2:11][CH2:10][CH2:9][CH2:8][CH2:7][C:6]=2[N:1]=[CH:2][N:3]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 24813Phosphorus oxychlorideHCID 178517909HCID 178517909, compound

Product 1

HCID 58199536HCID 58199536, compoundYield 98%

Conditions

Temperature
100 °C

Procedure

A mixture of 5,6,7,8,9,10-hexahydrocycloocta[d]-pyrimidine-4-ol (0.66 g; 3.7 mmol; 1.0 equiv) in 3.3 mL of POCl3 (37 mmol; 10 equiv) was heated at 100° C. for 2 hours. The reaction was cooled and poured onto ice. The solution was adjusted to ca. pH 5 with ammonium hydroxide. The oil was extracted with ether and the extract was dried over MgSO4. The solvent was evaporated to give 4-chloro-5,6,7,8,9,10-hexahydrocycloocta[d]-pyrimidine t as a clear yellow oil (0.71 g; 98% yield).

Workup

  1. temperatureThe reaction was cooled
  2. additionpoured onto ice
  3. extractionThe oil was extracted with ether
  4. dry with materialthe extract was dried over MgSO4
  5. customThe solvent was evaporated

Sources & evidence

ORD record
ord-94929ff5e3fb412c87eaec514ad4d434
Source dataset
uspto-grants-2013_07
Patent number
US08492373B2

Reaction notes

Loading…