HCID 19705215, compound → HCID 19705199, compound

HRID 727211Notes

Reaction equation

HRID 727211 reaction equation
[CH3:1][CH:2]1[CH:7]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH2:6][CH2:5][C:4](=O)[CH2:3]1.[C:15]([NH:17][C:18]([NH2:20])=[NH:19])#[N:16].NC1N=C(N)C2C[C@@H](C3C=CC=CC=3)[C@H](C)CC=2N=1>C(O)C>[NH2:16][C:15]1[C:3]2[CH:2]([CH3:1])[CH:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)[CH2:6][CH2:5][C:4]=2[N:19]=[C:18]([NH2:20])[N:17]=1

Participants

5

Reactant 3

HCID 19705215HCID 19705215, compoundHCID 86751976HCID 86751976, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 19705199HCID 19705199, compoundYield 13.8%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

The mixture of these isomers was prepared in a manner analogous to that of Example 1, using 7.0 grams (0.037 mole) of 3-methyl-4-phenylcyclohexanone and 3.4 grams (0.040 mole) of cyanoguanidine in ethoxyethoxy)ethanoethoxyethoxy)ethanol, yielding 1.3 grams of diamino-5-methyl-6-phenyl-5,6,7,8-tetrahydroquinazoline and cis/trans-2,4-diamino-7-methyl-6-phenyl-5,6,7,8-tetrahydroquinazoline. The NMR spectrum was consistent with the proposed structures. The cis/trans -2,4-diamino-5-methyl-6-phenyl-5,6,7,8-tetrahydroquinazoline is separated from cis/trans-2,4-diamino-7-methyl-6-phenyl-5,6,7,8-tetrahydroquinazoline by reverse phase high pressure liquid chromatography. The cis and trans geometric isomers of 2,4-diamino-5-methyl-6-phenyl-5,6,7,8-tetrahydroquinazoline and the cis and trans geometric isomers of 2,4-diamino-7-methyl-6-phenyl-5,6,7,8-tetrahydroquinazoline are also separated by reverse phase high pressure liquid chromatography.

Workup

  1. additionThe mixture of these isomers
  2. customwas prepared in a manner analogous to that of Example 1

Sources & evidence

ORD record
ord-7e8db998a43a4d3797fdcda61c72b6e6
Source dataset
uspto-grants-1998_01
Patent number
US05712281

Reaction notes

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