Isopropanol → HCID 22537289, compound
Reaction equation
[OH:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6]([OH:11])[N:5]=[CH:4][N:3]=1.[CH3:12][CH:13](O)[CH3:14].[C:16]1(P(C2C=CC=CC=2)C2C=CC=CC=2)[CH:21]=CC=C[CH:17]=1.N(C(OCC)=O)=NC(OCC)=O>O1CCCC1>[CH3:12][CH:13]([O:11][C:6]1[C:7]([N+:8]([O-:10])=[O:9])=[C:2]([O:1][CH:16]([CH3:21])[CH3:17])[N:3]=[CH:4][N:5]=1)[CH3:14]Participants
Procedure
To a mixture of 6.28 g of 4, 6-dihydroxy-5-nitropyrimidine, 6.00 g of 2-propanol, 10.5 g of triphenylphosphine and 80 ml of tetrahydrofuran was added 6.97 g of diethyl azodicarboxylate at room temperature with stirring, and the resultant mixture was stirred for 2 hours, mixed with 10.5 g of triphenylphosphine and 6.97 g of diethyl azodicarboxylate, stirred for 11 hours, again mixed with 10.5 g of triphenylphosphine and 6.97 g of diethyl azodicarboxylate and stirred for further 11 hours. The precipitate was filtered off, and the filtrate was concentrated in vacuo. The residue was mixed with ether, and the insoluble material was filtered off. The filtrate was concentrated in vacuo, and the residue was chromatographed on a silica gel column, eluting with ethyl acetate-n-hexane (1:14) to give 3.13 g of 4, 6-di (1-methylethoxy)-5-nitropyrimidine.
Workup
- stirringstirred for 11 hours
- stirringstirred for further 11 hours
- filtrationThe precipitate was filtered off
- concentrationthe filtrate was concentrated in vacuo
- additionThe residue was mixed with ether
- filtrationthe insoluble material was filtered off
- concentrationThe filtrate was concentrated in vacuo
- customthe residue was chromatographed on a silica gel column
- washeluting with ethyl acetate-n-hexane (1:14)
Sources & evidence
- ORD record
- ord-2d5b795aae05499fa31aada360bcc53a
- Source dataset
- uspto-grants-1995_08
- Patent number
- US05442060
Reaction notes
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