Tetrahydrofuran → HCID 13321944, compound

HRID 1284891Notes

Reaction equation

HRID 1284891 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+:19]([O-])=O)=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2].O1CCCC1>[C].[Pd].CO>[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]([NH2:19])=[CH:15][C:16]=3[C:17]=2[N:18]=1)=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 8028TetrahydrofuranHCID 13321943HCID 13321943, compound

Product 1

HCID 13321944HCID 13321944, compound

Reagents, catalysts & solvents 2

HCID 178418390HCID 178418390, compoundCatalystHCID 887MethanolSolvent

Procedure

1.5 g of 8-nitro-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester (Example 10) is hydrogenated in 90 ml of a mixture of equal parts of tetrahydrofuran and methanol at normal temperature under a hydrogen pressure of 70 bar, with the addition of 0.21 g of 10% palladiumcarbon. The solution, freed of catalyst, is evaporated, the residue is taken up in ethyl acetate and a small amount of ethanol, filtered, and evaporated to 3/4 its quantity, thus precipitating 0.400 g of 8-amino-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester, mp 256°-258° C.

Workup

  1. customis evaporated
  2. filtrationa small amount of ethanol, filtered
  3. customevaporated to 3/4 its quantity
  4. customthus precipitating 0.400 g of 8-amino-5H-pyrimido[5,4-b]indole-2-carboxylic acid ethyl ester, mp 256°-258° C.

Sources & evidence

ORD record
ord-9b39f4c152844e6fba8c149fb32d5c80
Source dataset
uspto-grants-1986_01
Patent number
US04564610

Reaction notes

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