Phosphorus oxychloride → HCID 18982115, compound

HRID 1463268Notes

Reaction equation

HRID 1463268 reaction equation
O[C:2]1[C:7]([NH:8][C:9]([C:11]2[O:12][CH:13]=[CH:14][CH:15]=2)=[O:10])=[C:6](O)[N:5]=[C:4]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:3]=1.P(Cl)(Cl)([Cl:30])=O>>[Cl:30][C:2]1[C:7]2[N:8]=[C:9]([C:11]3[O:12][CH:13]=[CH:14][CH:15]=3)[O:10][C:6]=2[N:5]=[C:4]([NH:17][CH2:18][CH2:19][C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=2)[N:3]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 178490296HCID 178490296, compound

Product 1

HCID 18982115HCID 18982115, compoundYield 83.2%

Conditions

Temperature
90 °C

Procedure

A mixture of 4,6-dihydroxy-5-(2-furanylcarbonyl)amino-2-[(4-methoxyphenyl)ethyl]aminopyrimidine (408 mg) and phosphorus oxychloride (5 ml) was heated at 90° C. for 3 hours. The excess phosphorus oxychloride was removed by evaporation, in vacuo, and then by azeotroping with toluene (2×50 ml). The residue was added to water and the resultant precipitate filtered off, washed with water and dried. There was thus produced 7-chloro-2-(2-furyl)-5-[2-(4-methoxyphenyl)ethyl]amino oxazolo[5,4-d]pyrimidine (340 mg, 83.2% yield); m.p. 169.5°-171° C.: NMR:DMSO-d6 : 2.80(t, 2H, ArCH2), 3.48(q, 2H, CH2NH), 3.72(s, 3H, OMe), 6.80(m, 1H, furyl-H), 6.85(d, 2H, ArH), 7.16(d, 2H, ArH), 7.44(d, 1H, furyl-H), 8.07(m, 1H, furyl-H), 8.13(brs, 1H, NH).

Workup

  1. customThe excess phosphorus oxychloride was removed by evaporation, in vacuo
  2. customby azeotroping with toluene (2×50 ml)
  3. additionThe residue was added to water
  4. filtrationthe resultant precipitate filtered off
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-895bb94d256a4c988d489b973216ad70
Source dataset
uspto-grants-1994_04
Patent number
US05300509

Reaction notes

Loading…