Sulfur → HCID 15718805, compound

HRID 2166128Notes

Reaction equation

HRID 2166128 reaction equation
[CH2:1]([O:3][CH2:4][CH2:5][NH:6][C:7]1[C:12]([NH:13][C:14]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=S)=[CH:11][N:10]=[CH:9][N:8]=1)[CH3:2].[S]>[Hg]=O.O1CCCC1>[CH2:1]([O:3][CH2:4][CH2:5][N:6]1[C:14]([NH:16][CH:17]2[CH2:22][CH2:21][N:20]([CH2:23][C:24]3[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=3)[CH2:19][CH2:18]2)=[N:13][C:12]2[C:7]1=[N:8][CH:9]=[N:10][CH:11]=2)[CH3:2]

Participants

5

Reactant 2

HCID 5362487SulfurHCID 15718804HCID 15718804, compound

Product 1

HCID 15718805HCID 15718805, compoundYield 79.3%

Reagents, catalysts & solvents 2

HCID 30856Mercuric oxideCatalystHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 22.4 parts of N-[4-[(2-ethoxyethyl)amino]-5-pyrimidinyl]-N'-[1-(phenylmethyl)-4-piperidinyl]thiourea, 17.3 parts of mercury(II) oxide, 0.1 parts of sulfur and 270 parts of tetrahydrofuran was stirred for 2 hours at reflux temperature. The reaction mixture was filtered while hot over diatomaceous earth. The filtrate was evaporated and the residue was purified by column chromatography over silica gel using a mixture of trichloromethane and methanol (95:5 by volume) as eluent. The pure fractions were collected and the eluent was evaporated, yielding 16.3 parts (79.3%) of 9-(2-ethoxyethyl)-N-[1-(phenylmethyl)-4-piperidinyl]-9H-purin-8-amine as a residue (compound 11).

Workup

  1. temperatureat reflux temperature
  2. filtrationThe reaction mixture was filtered while hot over diatomaceous earth
  3. customThe filtrate was evaporated
  4. customthe residue was purified by column chromatography over silica gel using
  5. additiona mixture of trichloromethane and methanol (95:5 by volume) as eluent
  6. customThe pure fractions were collected
  7. customthe eluent was evaporated

Sources & evidence

ORD record
ord-ff09e3862f2f4f5383fd637c2b079bb2
Source dataset
uspto-grants-1990_07
Patent number
US04943580

Reaction notes

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