Potassium Carbonate → HCID 15571590, compound

HRID 127928Notes

Reaction equation

HRID 127928 reaction equation
Cl.[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([OH:19])[CH:12]=2)=[CH:5][N:4]=1.Br[CH2:21][CH2:22][CH2:23][NH:24][S:25](=[O:37])([C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:36])[CH3:35])=[CH:29][CH:28]=1)=[O:26].C([O-])([O-])=O.[K+].[K+]>CN(C)C=O>[NH2:2][C:3]1[N:8]=[C:7]([NH2:9])[C:6]([CH2:10][C:11]2[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[C:13]([O:19][CH2:21][CH2:22][CH2:23][NH:24][S:25](=[O:26])([C:27]3[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:36])[CH3:35])=[CH:29][CH:28]=3)=[O:37])[CH:12]=2)=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 15571588HCID 15571588, compoundHCID 18552221HCID 18552221, compound

Product 1

HCID 15571590HCID 15571590, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of 2.82 g (0.01 mole) of 2,4-diamino-5-(3'-hydroxy-4'-methoxybenzyl)pyrimidine hydrochloride, 3.36 g (0.01 mole) of N1 -(3-bromopropyl)-N4 -acetylsulfanilamide, 2.76 g of anhydrous K2CO3, and 20 ml of dimethylformamide is heated with stirring at 100° for 18 hr. The mixture is concentrated in vacuo to a dark oil, which is shaken with a mixture of water and chloroform. The oily material which remaines insoluble in the water and chloroform is chromatographed on silica gel. Elution with chloroform-methanol, (85:15) gives fractions containing 0.55 g (11%) of 2,4-diamino-5-{3'-[3"-(N4 -acetylsulfanilamido)propoxy-4'-methoxybenzyl}pyrimidine, m.p. 96°-98°. Spectral data are consistent with the proposed structure.

Workup

  1. temperatureis heated
  2. concentrationThe mixture is concentrated in vacuo to a dark oil, which
  3. stirringis shaken with a mixture of water and chloroform
  4. customis chromatographed on silica gel
  5. washElution with chloroform-methanol, (85:15)
  6. customgives fractions

Sources & evidence

ORD record
ord-fa0d9b4675454867970a898b72bddf57
Source dataset
uspto-grants-1981_03
Patent number
US04258045

Reaction notes

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