Isoamyl Nitrite → HCID 13321952, compound

HRID 1284899Notes

Reaction equation

HRID 1284899 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14](N)=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2].N(OCCC(C)C)=O.[CH3:28][S:29]SC>>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[CH:8][C:9]2[NH:10][C:11]3[CH:12]=[CH:13][C:14]([S:29][CH3:28])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2]

Participants

4

Reactant 3

HCID 8053Isoamyl NitriteHCID 12232Dimethyl DisulfideHCID 13321944HCID 13321944, compound

Product 1

HCID 13321952HCID 13321952, compound

Procedure

400 mg of 8-amino-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester (Example 11) is heated in 4.8 ml of dimethyl disulfide under argon to 60° C. The mixture is then combined with 2.8 ml of isoamyl nitrite and heated for one hour to 80° C. After evaporation, the mixture is chromatographed over silica gel with methylene chloride/ethanol=10:1 as the eluent. Recrystallization of the corresponding fractions yields 130 mg of 8-methylthio-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester, mp 265°-266° C.

Workup

  1. temperatureheated for one hour to 80° C
  2. customAfter evaporation
  3. customthe mixture is chromatographed over silica gel with methylene chloride/ethanol=10:1 as the eluent
  4. customRecrystallization of the corresponding fractions

Sources & evidence

ORD record
ord-9196d4a4eb6041d8b201c0914ecb7867
Source dataset
uspto-grants-1986_01
Patent number
US04564610

Reaction notes

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