Chlorotrimethylsilane → HCID 12953067, compound

HRID 1577418Notes

Reaction equation

HRID 1577418 reaction equation
Cl[Si](C)(C)C.[O:6]=[C:7]1[N:12]2[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:11]2=[N:10][C:9]2[CH2:20][CH2:21][S:22][C:8]1=2.ClN1C(=O)CCC1=O>N1C=CC=CC=1>[O:6]=[C:7]1[N:12]2[CH:13]=[C:14]([C:17]([OH:19])=[O:18])[CH:15]=[CH:16][C:11]2=[N:10][C:9]2=[CH:8][S:22][CH:21]=[C:20]12

Participants

5

Reactant 3

HCID 6397ChlorotrimethylsilaneHCID 31398ChlorosuccinimideHCID 12953046HCID 12953046, compound

Product 1

HCID 12953067HCID 12953067, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

Chlorotrimethylsilane (2.35 ml, 0.018 mol) is added to a cooled (ice bath) solution of 3,10-dihydro-10-oxo-1H-pyrido[1,2-a]-thieno[3,2-d]pyrimidine-7-carboxylic acid (4.5 g, 0.018 mol) in pyridine (35 ml) under nitrogen. The mixture is stirred at ice bath temperature for 1 hour and then allowed to warm at room temperature. N-chlorosuccinimide (2.44 g, 0.018 mol) is added and the mixture is heated at 95° C. for 20 minutes. The mixture is cooled, diluted with ice water (5 ml) and stirred for 15 minutes. The precipitate is filtered, washed with boiling acetone and dried to give the product (3.5 g.) mp 335° C. (dec).

Workup

  1. temperaturethe mixture is heated at 95° C. for 20 minutes
  2. temperatureThe mixture is cooled
  3. stirringstirred for 15 minutes
  4. filtrationThe precipitate is filtered
  5. washwashed with boiling acetone
  6. customdried
  7. customto give the product (3.5 g.) mp 335° C. (dec)

Sources & evidence

ORD record
ord-e85d0e535b734a2f89094bd4941e71d0
Source dataset
uspto-grants-1981_09
Patent number
US04287340

Reaction notes

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