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

HRID 1658269Notes

Reaction equation

HRID 1658269 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-69225a11ac464ea9bd26cafbcfff2208
Source dataset
uspto-grants-1976_06
Patent number
US03963718

Reaction notes

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