5-(Bromomethyl)-2-ethyl-4-pyrimidinamine Hydrobromide → 6-[(4-Amino-2-ethyl-5-pyrimidinyl)methyl]-2,7-dimethylthieno[2,3-c]pyridinium bromide hydrobromide

HRID 435775Notes

Reaction equation

HRID 435775 reaction equation
[BrH:1].[CH2:2]([C:4]1[N:9]=[C:8]([NH2:10])[C:7]([CH2:11][Br:12])=[CH:6][N:5]=1)[CH3:3].[CH3:13][C:14]1[S:23][C:17]2=[C:18]([CH3:22])[N:19]=[CH:20][CH:21]=[C:16]2[CH:15]=1>CN(C)C=O>[BrH:12].[Br-:1].[NH2:10][C:8]1[C:7]([CH2:11][N+:19]2[C:18]([CH3:22])=[C:17]3[S:23][C:14]([CH3:13])=[CH:15][C:16]3=[CH:21][CH:20]=2)=[CH:6][N:5]=[C:4]([CH2:2][CH3:3])[N:9]=1

Participants

4

Reactant 2

HCID 214166655-(Bromomethyl)-2-ethyl-4-pyrimidinamine HydrobromideHCID 214166792,7-Dimethylthieno[2,3-c]pyridine

Product 1

HCID 214166766-[(4-Amino-2-ethyl-5-pyrimidinyl)methyl]-2,7-dimethylthieno[2,3-c]pyridinium bromide hydrobromideYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

891 Mg. of 2-ethyl-4-amino-5-bromomethyl pyrimidine hydrobromide is dissolved in 5 ml. of dimethylformamide (DMF), 1.95 g. of 2,7-dimethylthieno[2,3-c]-pyridine is added; a precipitate forms immediately. The precipitate is collected, washed with DMF, and discarded. The filtrates are stirred at room temperature overnight, diluted with ether, and the off-white precipitate collected and washed with ether. The solid is dissolved in methanol, hydrogen bromide gas introduced, and the colorless product isolated from methanol-isopropanol. 270 Mg. of product, 6-[(4-amino-2-ethyl-5-pyrimidinyl)methyl]-2,7-dimethylthieno[2,3-c]pyridinium bromide hydrobromide is recovered, m.p. 215°-216° C., dec., 20% yield.

Workup

  1. customThe precipitate is collected
  2. washwashed with DMF
  3. additiondiluted with ether
  4. customthe off-white precipitate collected
  5. washwashed with ether
  6. dissolutionThe solid is dissolved in methanol
  7. additionhydrogen bromide gas introduced
  8. customthe colorless product isolated from methanol-isopropanol
  9. customof product, 6-[(4-amino-2-ethyl-5-pyrimidinyl)methyl]-2,7-dimethylthieno[2,3-c]pyridinium bromide hydrobromide is recovered

Sources & evidence

ORD record
ord-8c7adbfdaf8345be8a9b9a32af95a93b
Source dataset
uspto-grants-1977_02
Patent number
US04006143

Reaction notes

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