P-Cresol → 3-(2-tetrahydropyranyl)-1,2,3,4,6,7-hexahydro-1-(p-tolyloxycarbonyl)-5H-cyclopentapyrimidine-2,4-dione

HRID 2290682Notes

Reaction equation

HRID 2290682 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:12](=[O:13])[C:11]2[CH2:14][CH2:15][CH2:16][C:10]=2[NH:9][C:8]1=[O:17].[H-].[Na+].Cl[C:21]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=1)=[O:22].C1C(O)=CC=C(C)C=1.C(OC(C)C)(C)C>O.CN(P(N(C)C)(N(C)C)=O)C.O1CCCC1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[N:7]1[C:12](=[O:13])[C:11]2[CH2:14][CH2:15][CH2:16][C:10]=2[N:9]([C:21]([O:23][C:24]2[CH:29]=[CH:28][C:27]([CH3:30])=[CH:26][CH:25]=2)=[O:22])[C:8]1=[O:17]

Participants

9

Reactant 5

HCID 2879P-CresolHCID 7914Diisopropyl EtherHCID 24758Sodium hydrideHCID 70304p-Tolyl chloroformateHCID 134553853-(2-tetrahydropyranyl)-1,2,3,4,6,7-hexahydro-5H-cyclopentapyrimidine-2,4-dione

Product 1

HCID 134553863-(2-tetrahydropyranyl)-1,2,3,4,6,7-hexahydro-1-(p-tolyloxycarbonyl)-5H-cyclopentapyrimidine-2,4-dioneYield 65.9%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolventHCID 12679HexamethylphosphoramideSolvent

Procedure

15 g of 3-(2-tetrahydropyranyl)-1,2,3,4,6,7-hexahydro-5H-cyclopentapyrimidine-2,4-dione [prepared according to the French Pat. No. 2,029,250] were introduced with stirring over 20 minutes at 20° C. into 130 ml of anhydrous tetrahydrofuran and 13 ml of hexamethylphosphotriamide and then 3.35 g of a 50% suspension of sodium hydride in oil were introduced in several portions at 0° C. with stirring for 105 minutes. Then 13 g of p-tolyl chloroformate prepared from p-cresol were introduced dropwise with stirring at 20° C. over 17 hours and the mixture was then poured into iced water. Isopropyl ether was added thereto and the mixture was vacuum filtered. The solid product was dried to obtain 15.5 g of 3-(2-tetrahydropyranyl)-1,2,3,4,6,7-hexahydro-1-(p-tolyloxycarbonyl)-5H-cyclopentapyrimidine-2,4-dione melting at 136° C.

Workup

  1. addition2,029,250] were introduced
  2. additionwere introduced dropwise
  3. stirringwith stirring at 20° C. over 17 hours
  4. filtrationfiltered
  5. customThe solid product was dried

Sources & evidence

ORD record
ord-b4da4891f83342a29b12e2452f15c2d2
Source dataset
uspto-grants-1986_10
Patent number
US04618364

Reaction notes

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