Methane → 2,4-Diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine Citrate

HRID 34443

Reaction equation

HRID 34443 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[C:15]3[CH:16]=[CH:17][CH2:18][O:19][C:14]=3[C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=2)=[CH:4][N:3]=1.O.[C:25]([OH:37])(=[O:36])[CH2:26][C:27]([CH2:32][C:33]([OH:35])=[O:34])([C:29]([OH:31])=[O:30])[OH:28].C>CO>[C:25]([OH:37])(=[O:36])[CH2:26][C:27]([CH2:32][C:33]([OH:35])=[O:34])([C:29]([OH:31])=[O:30])[OH:28].[NH2:1][C:2]1[N:7]=[C:6]([NH2:8])[C:5]([CH2:9][C:10]2[C:15]3[CH:16]=[CH:17][CH2:18][O:19][C:14]=3[C:13]([O:20][CH3:21])=[C:12]([O:22][CH3:23])[CH:11]=2)=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 297MethaneHCID 222302-Hydroxy-1,2,3-propanetricarboxylic acid hydrate (1:1)HCID 128497722,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine

Product 1

HCID 201297832,4-Diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine CitrateYield 99.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To 2,4-diamino-5-(7,8-dimethoxy-2H-1-benzopyran-5-ylmethyl)pyrimidine (5.00 g, 15.9 mmol) in 450 mL of boiling methanol was added a solution of citric acid monohydrate (3.34 g, 15.9 mmol) in 50 mL of methanol. The solution was treated with charcoal, filtered, and evaporated to dryness. Further drying at 40° C. in a vacuum oven gave 8.01 g (99.5%) of the title compound. Karl Fisher analysis: 5.3% H2O. Anal. Calcd for C16H18N4O3.C6H8O7.1.5H2O: C, 49.53; H, 5.48; N, 10.50. Found: C, 49.54; H, 5.49; N, 10.47.

Workup

  1. filtrationfiltered
  2. customevaporated to dryness
  3. customFurther drying at 40° C. in a vacuum oven

Sources & evidence

ORD record
ord-27c1df14c2bf48e0966f9cafb3f8d0c3
Source dataset
uspto-grants-1988_08
Patent number
US04761475

Linked notes

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