Imidazole → 2-(Imidazol-1-yl)-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidine

HRID 2302385Notes

Reaction equation

HRID 2302385 reaction equation
Cl[C:2]1[N:3]=[C:4]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:5]2[CH:10]=[C:9]([CH3:11])[S:8][C:6]=2[N:7]=1.[NH:23]1[CH:27]=[CH:26][N:25]=[CH:24]1.C1(O)C=CC=CC=1>>[N:23]1([C:2]2[N:3]=[C:4]([NH:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:5]3[CH:10]=[C:9]([CH3:11])[S:8][C:6]=3[N:7]=2)[CH:27]=[CH:26][N:25]=[CH:24]1

Participants

4

Reactant 3

HCID 795ImidazoleHCID 996PhenolHCID 109585612-Chloro-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno-[2,3-d]pyrimidine

Product 1

HCID 98420552-(Imidazol-1-yl)-6-methyl-4-(3,4-methylenedioxybenzylamino)thieno[2,3-d]pyrimidineYield 184.9%

Procedure

A solution of 2-chloro-6-methyl-4-(3,4-methylene dioxybenzylamino)-thieno-[2,3-d]-pyrimidine (1.67 g), imidazole (1.02 g) and phenol (2 g) are heated 5 hours at 150° C. After cooling, the residue is dissolved in C2Cl2. The solvent is removed, and the usual workup yields 2-(imidazol-1-yl)-6-methyl-4-(3,4-methylenedioxybenzylamino)-thieno-[2,3-d]-pyrimidine (3.38 g) Mp. 162° C.

Workup

  1. temperatureAfter cooling
  2. dissolutionthe residue is dissolved in C2Cl2
  3. customThe solvent is removed

Sources & evidence

ORD record
ord-2b4250c3765a42eebf11b78ccfd2f552
Source dataset
uspto-grants-2002_08
Patent number
US06432950B1

Reaction notes

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