Ammonium Hydroxide → 2,4-Diamino-5-(7,8-dimethoxy-2-oxo-2H-1-benzopyran-5-ylmethyl)pyrimidine

HRID 34447

Reaction equation

HRID 34447 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[CH:15]=[C:14]([O:16][CH3:17])[C:13]([O:18][CH3:19])=[C:12]([OH:20])[CH:11]=2)=[CH:4][N:3]=1.[CH2:21](C(O)=O)[C@H:22](O)[C:23](O)=[O:24].[OH-].[NH4+]>>[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[C:11]3[CH:21]=[CH:22][C:23](=[O:24])[O:20][C:12]=3[C:13]([O:18][CH3:19])=[C:14]([O:16][CH3:17])[CH:15]=2)=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 14923Ammonium HydroxideHCID 222656L-Malic AcidHCID 128497693-Demethyltrimethoprim

Product 1

HCID 128498002,4-Diamino-5-(7,8-dimethoxy-2-oxo-2H-1-benzopyran-5-ylmethyl)pyrimidine

Procedure

A mixture of 1.38 g (0.005 mole) of 2,4-diamino-5-(3-hydroxy-4,5-dimethoxybenzyl)pyrimidine and 1.01 g (0.0075 mole) of L-(-)-malic acid in polyphosphoric acid (30 g) was heated at 90°-100° for 4 hours. The resulting clear syrup was poured into ice-water (150 mL) and basified (pH 8) with conc'd ammonium hydroxide. The title compound was filtered off and washed with ethanol. Yield, 0.26 g (16%); m.p. 278°-280° dec; structure confirmed by 13C and 1H NMR and mass spectra. Anal. Calcd. for C16H18N4O3 : C, 58.53; H, 4.91; N, 17.07. Found: C, 58.27; H, 4.99; N, 16.97.

Workup

  1. temperaturewas heated at 90°-100° for 4 hours
  2. filtrationThe title compound was filtered off
  3. washwashed with ethanol
  4. customYield

Sources & evidence

ORD record
ord-d25e86c760204dabbd239e339cb2dee5
Source dataset
uspto-grants-1988_08
Patent number
US04761475

Linked notes

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