Sodium Methoxide → 2-Ethylamino-4-amino-6-methyl-5-[3-(4-chlorophenyl)-2-butenyl]pyrimidine

HRID 54261Notes

Reaction equation

HRID 54261 reaction equation
Cl.[CH2:2]([NH:4][C:5]([NH2:7])=[NH:6])[CH3:3].[C:8]([C:10]([CH2:19][CH:20]=[C:21]([C:23]1[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=1)[CH3:22])=[C:11](OCCCCC)[CH3:12])#[N:9].[C:30]([C:32]([CH2:41][CH2:42][C:43]([C:45]1[CH:50]=[CH:49][C:48]([Cl:51])=[CH:47][CH:46]=1)=[CH2:44])=[C:33](OCCCCC)[CH3:34])#[N:31].C[O-].[Na+]>C(O)C.CN(C)C(=O)C>[CH2:2]([NH:4][C:5]1[N:7]=[C:8]([NH2:9])[C:10]([CH:19]=[CH:20][CH:21]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)[CH3:22])=[C:11]([CH3:12])[N:6]=1)[CH3:3].[CH2:2]([NH:4][C:5]1[N:7]=[C:30]([NH2:31])[C:32]([CH2:41][CH:42]=[C:43]([C:45]2[CH:46]=[CH:47][C:48]([Cl:51])=[CH:49][CH:50]=2)[CH3:44])=[C:33]([CH3:34])[N:6]=1)[CH3:3]

Participants

8

Reactant 4

HCID 10942334Sodium MethoxideHCID 542041083-Cyano-2-pentoxy-6-(4-chlorophenyl)-2,5-heptadieneHCID 545746983-Cyano-2-pentoxy-6-(4-chlorophenyl)-2,6-heptadieneHCID 178464621HCID 178464621, compound

Product 2

HCID 537347202-Ethylamino-4-amino-6-methyl-5-[3-(4-chlorophenyl)-2-butenyl]pyrimidineHCID 540338362-Ethylamino-4-amino-6-methyl-5-[3-(4-chlorophenyl)-1-butenyl]pyrimidine

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 31374DimethylacetamideSolvent

Procedure

These compounds are prepared in a manner analogous to that of Step E of Example 1, using 4.8 grams (0.039 mole) of 1-ethylguanidine hydrochloride, 3.6 grams (0.011 mole) of a mixture of 3-cyano-2-pentoxy-6-(4-chlorophenyl)-2,5-heptadiene and 3-cyano-2-pentoxy-6-(4-chlorophenyl)-2,6-heptadiene (prepared in Steps A-D of Example 1), 2.3 grams (0.039 mole) of sodium methoxide, 20 mL of N,N-dimethylacetamide, and 40 mL of ethanol. The crude reaction product is subjected to column chromatography, yielding the separated isomers, 2-ethylamino-4-amino-6-methyl-5-[3-(4-chlorophenyl)-1-butenyl]pyrimidine (Compound 47) and 2-ethylamino-4-amino-6-methyl-5-[3-(4-chlorophenyl)-2-butenyl]pyrimidine.

Workup

  1. customThese compounds are prepared in a manner analogous to that of Step E of Example 1
  2. customThe crude reaction product

Sources & evidence

ORD record
ord-528f980a809141debb52fdbaf740b200
Source dataset
uspto-grants-1997_04
Patent number
US05622954

Reaction notes

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