Ammonium Hydroxide → HCID 23321130, compound

HRID 280700Notes

Reaction equation

HRID 280700 reaction equation
[CH2:1]([C:4]1[C:18]([OH:19])=[C:17]([O:20][CH3:21])[C:16]([O:22][CH3:23])=[CH:15][C:5]=1[CH2:6][C:7]1[C:8]([NH2:14])=[N:9][C:10]([NH2:13])=[N:11][CH:12]=1)[CH:2]=[CH2:3].[OH-].[NH4+]>>[NH2:13][C:10]1[N:9]=[C:8]([NH2:14])[C:7]([CH2:6][C:5]2[C:4]3[CH2:1][CH:2]([CH3:3])[O:19][C:18]=3[C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)=[CH:12][N:11]=1

Participants

3

Reactant 2

HCID 14923Ammonium HydroxideHCID 23321125HCID 23321125, compound

Product 1

HCID 23321130HCID 23321130, compoundYield 80%

Procedure

A mixture of 5-(2-allyl-3-hydroxy-4,5-dimethoxybenzyl)-2,4-diaminopyrimidine (1.50 g, 4.74 mmol) and polyphosphoric acid (50 g) was heated to 95° and maintained at this temperature with stirring until a clear pale yellow syrup was achieved (about 1 h). This syrup was poured into ice-water and the resulting solution basified with ammonium hydroxide. The resulting white solid (1.3 g) was chromatographed on silica gel eluted with MeOH:CH2Cl2 /1:9 to give the title compound as white powder (1.2 g). Recrystallization from 95% ethanol gave clusters of white needles, mp 216°-219°. Anal. Calcd for C16H20N4O3 (316.37); C, 60.74; H, 6.37; N, 17.71. Found: C, 60.48; H, 6.41; N, 17.63.

Workup

  1. temperaturewas heated to 95°
  2. temperaturemaintained at this temperature
  3. custom(about 1 h)
  4. customThe resulting white solid (1.3 g) was chromatographed on silica gel
  5. washeluted with MeOH

Sources & evidence

ORD record
ord-3a3c855506044b24b4a72c2dd4488c4d
Source dataset
uspto-grants-1986_05
Patent number
US04590271

Reaction notes

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