Sodium Methoxide → 6-Acetyl-2-butyl-5,6,7,8-tetrahydro-pyrido-[4,3-d]pyrimidin-4(3H)-one

HRID 1198463

Reaction equation

HRID 1198463 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][C:7](=O)[CH:6]([C:11]([O:13]CC)=O)[CH2:5]1)(=[O:3])[CH3:2].Cl.[C:17]([NH2:23])(=[NH:22])[CH2:18][CH2:19][CH2:20][CH3:21].C[O-].[Na+]>C(O)C.CO>[C:1]([N:4]1[CH2:9][CH2:8][C:7]2[N:22]=[C:17]([CH2:18][CH2:19][CH2:20][CH3:21])[NH:23][C:11](=[O:13])[C:6]=2[CH2:5]1)(=[O:3])[CH3:2]

Participants

6

Reactant 3

HCID 10942334Sodium MethoxideHCID 11615174Pentanimidamide HydrochlorideHCID 12445847Ethyl 1-acetyl-4-oxo-3-piperidinecarboxylate

Product 1

HCID 1360140346-Acetyl-2-butyl-5,6,7,8-tetrahydro-pyrido-[4,3-d]pyrimidin-4(3H)-oneYield 96.9%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 887MethanolSolvent

Procedure

A mixture of 1.5 g of ethyl 1-acetyl-4-oxo-3-piperidinecarboxylate and 1.0 g of valeramidine hydrochloride in 15 ml of anhydrous ethyl alcohol is treated with 7.5 ml of a 1M solution of sodium methoxide in methanol. The resulting mixture is stirred and heated at reflux for one hour. The reaction mixture is allowed to cool over 30 minutes then filtered. The filtrate is evaporated to a colorless syrup which is stirred with 50 ml of ether for 2 hours then filtered. The tacky cake is dried under high vacuum at 56° C. to afford 1.7 g of the desired product, m.p. 106°-113° C.

Workup

  1. temperatureheated
  2. temperatureat reflux for one hour
  3. temperatureto cool over 30 minutes
  4. filtrationthen filtered
  5. customThe filtrate is evaporated to a colorless syrup which
  6. stirringis stirred with 50 ml of ether for 2 hours
  7. filtrationthen filtered
  8. customThe tacky cake is dried under high vacuum at 56° C.

Sources & evidence

ORD record
ord-2c365a98f2c74fdbbaf1488ebff5bce4
Source dataset
uspto-grants-1994_01
Patent number
US05281602

Linked notes

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