Sulfuric Acid → 4-Phenyl-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine

HRID 1576855Notes

Reaction equation

HRID 1576855 reaction equation
[NH:1]1[CH2:6][CH2:5][CH2:4][N:3]=[C:2]1[NH:7][CH2:8][CH2:9][CH:10](O)[C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.S(=O)(=O)(O)O.[OH-].[Na+]>>[C:11]1([CH:10]2[N:3]3[CH2:4][CH2:5][CH2:6][N:1]=[C:2]3[NH:7][CH2:8][CH2:9]2)[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 21510116HCID 21510116, compound

Product 1

HCID 215101174-Phenyl-1,3,4,6,7,8-hexahydro-2H-pyrimido[1,2-a]pyrimidine

Procedure

A mixture of 2 parts of α-[2-(1,4,5,6-tetrahydro-2-pyrimidinylamino)ethyl]benzylalcohol and 27 parts of sulfuric acid 80% is stirred for 2 hours at room temperature. The reaction mixture is poured onto crushed ice and the whole is alkalized with sodium hydroxide solution. The product is extracted with toluene. The organic layer is separated, dried, filtered and evaporated. The solid residue is crystallized from acetone, yielding 3,4,6,7,8,9-hexahydro-6-phenyl-2H-pyrimido-[1,2-a]pyrimidine, m.p. 177°-179°C.

Workup

  1. additionThe reaction mixture is poured
  2. customonto crushed ice
  3. extractionThe product is extracted with toluene
  4. customThe organic layer is separated
  5. customdried
  6. filtrationfiltered
  7. customevaporated
  8. customThe solid residue is crystallized from acetone

Sources & evidence

ORD record
ord-02dccde1fa324927a76bc4e1f1c7d368
Source dataset
uspto-grants-1976_09
Patent number
US03983133

Reaction notes

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