Chlorotrimethylsilane → HCID 178496382, compound

HRID 1447149Notes

Reaction equation

HRID 1447149 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([C:15]([OH:17])=[O:16])=[CH:10][N:9]=2)=[CH:4][CH:3]=1.C(N(CC)CC)C.Cl[Si](C)(C)C.[CH3:30][O:31][CH2:32][C:33](Cl)=[O:34]>ClCCl.CO.O>[CH3:30][O:31][CH2:32][C:33]([NH:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:13]=[C:12]([OH:14])[C:11]([C:15]([OH:17])=[O:16])=[CH:10][N:9]=2)=[CH:6][CH:7]=1)=[O:34]

Participants

8

Reactant 4

HCID 6397ChlorotrimethylsilaneHCID 8471TriethylamineHCID 96623Methoxyacetyl chlorideHCID 178507442HCID 178507442, compound

Product 1

HCID 178496382HCID 178496382, compoundYield 90.1%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 6.9 g (30 mmol) of 2-(4-aminophenyl)-4-hydroxy-5-pyrimidine carboxylic acid and 400 ml of dichloromethane is stirred at room temperature and 16.6 ml (120 mmol) of triethylamine is added followed by 11.3 ml (90 mmol) of chlorotrimethylsilane. The mixture is stirred at room temperature for 30 min and 3.2 ml (30 mmol) of methoxyacetyl chloride in 10 ml of dichloromethane is added dropwise at 0°. The resulting mixture is stirred for 18 hrs at room temperature and 15 ml of water and 50 ml of methanol are added. The solid is filtered, washed, and dried to give 8.2 g of 2-[4-(methoxyacetylamino)phenyl]-4-hydroxy-5-pyrimidine carboxylic acid. An additional 3.2 g is obtained by evaporation of the filtrate. After recrystallization from dimethyl sulfoxide-water, the material has mp 297°-300° dec.

Workup

  1. stirringThe mixture is stirred at room temperature for 30 min
  2. stirringThe resulting mixture is stirred for 18 hrs at room temperature
  3. filtrationThe solid is filtered
  4. washwashed
  5. customdried

Sources & evidence

ORD record
ord-af9ea36fcb9a4590aafb047820fc749b
Source dataset
uspto-grants-1982_02
Patent number
US04315933

Reaction notes

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