Ammonia → HCID 9884818, compound

HRID 1463266Notes

Reaction equation

HRID 1463266 reaction equation
Cl[C:2]1[C:3]2[N:21]=[C:20]([C:22]3[O:23][CH:24]=[CH:25][CH:26]=3)[O:19][C:4]=2[N:5]=[C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:7]=1.[Cl-].[NH4+:28].N.O>C(O)C>[NH2:28][C:2]1[C:3]2[N:21]=[C:20]([C:22]3[O:23][CH:24]=[CH:25][CH:26]=3)[O:19][C:4]=2[N:5]=[C:6]([NH:8][CH2:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=2)[N:7]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 962WaterHCID 25517Ammonium ChlorideHCID 18982115HCID 18982115, compound

Product 1

HCID 9884818HCID 9884818, compoundYield 48.6%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
100 °C

Procedure

7-chloro-2-(2-furyl)-5-[2-(4-methoxyphenyl)ethyl]amino-oxazolo[5,4-d]pyrimidine (0.5 g) and ammonium chloride (0.1 g) were added to a saturated solution of ammonia in ethanol (20 ml) and sealed in a Caries tube. The sealed tube was then heated at 100° C. for 18 hours. The cooled reaction mixture was poured into water (200 ml) and the resultant precipitate removed by filtration. The solid was recrystallised from methanol to afford 7-amino-2-(2-furyl)-5-[2-(4-methoxyphenyl)ethyl]amino-oxazolo[5,4-d]pyrimidine (0.23 g, 48.6%), m.p. 194°-196° C.; microanalysis, found: C, 61.5; H, 4.8; N, 19.5%; C18H17N5O3 requires: C, 61.5; H, 4.9; N, 19.9%; NMR (DMSO-d6); 2.76(t,2H ArCH2), 3.44(brq 2H, CH2NH), 3.72(s, 3H, OMe), 6.70(m, 1 H furyl-H), 6.28(brs, 1H NH), 6.84(d, 2H, ArH), 7.13(complex, 5H ArH, NH2 furyl-H), 7.89(m, 1H, furyl-H); m/e [M+H]+ 352.

Workup

  1. customsealed in a Caries tube
  2. customThe cooled reaction mixture
  3. customthe resultant precipitate removed by filtration
  4. customThe solid was recrystallised from methanol

Sources & evidence

ORD record
ord-3e7f895a1248418eac9c51eee304611d
Source dataset
uspto-grants-1994_04
Patent number
US05300509

Reaction notes

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