Diethyl Ether → 3-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

HRID 1878440Notes

Reaction equation

HRID 1878440 reaction equation
[Cl:1][CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH:14]([O:15]CC3C=CC=CC=3)[C:7]2=[N:6][C:5]=1[CH3:23].[H][H].C(OCC)C>Cl.[Pd].C(N(CC)CC)C.CO.CCCCCC>[Cl:1][CH2:2][CH2:3][C:4]1[C:9](=[O:10])[N:8]2[CH2:11][CH2:12][CH2:13][CH:14]([OH:15])[C:7]2=[N:6][C:5]=1[CH3:23]

Participants

9

Reactant 3

HCID 3283Diethyl EtherHCID 44140429HCID 44140429, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 155471943-(2-Chloroethyl)-6,7,8,9-tetrahydro-9-hydroxy-2-methyl-4H-pyrido[1,2-a]pyrimidin-4-one

Reagents, catalysts & solvents 5

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 887MethanolSolvent2×HCID 8058HexaneSolventHCID 8471TriethylamineSolvent

Procedure

At room temperature, 3-(2-chloroethyl)-2-methyl-9-benzyloxy-6,7,8,9-tetrahydro-pyrido[1,2-a]pyrimidin-4-one 4.0 g (0.0122 mole) was charged into a 250 mL three-necked bottle, 80 mL methanol was added, and then concentrated hydrochloric acid (about 25 drops) was added dropwise with stirring to adjust pH to 3.0. After the dissolution was completed, 1.8 g of wet 5% Pd—C (water content: 56%) (W/W: 10/1) was added, argon gas was fed to exchange atmosphere for three times, hydrogen gas was fed to exchange atmosphere for three times, the reaction was conducted at 27° C. for about 36 hours, and TLC (ethyl ether:n-hexane:methanol:triethylamine=2 mL:0.5 mL:6 drops:6 drops) was used to detect the debenzylated product. The reaction was stopped after all starting materials were consumed.

Workup

  1. additionwas added
  2. dissolutionAfter the dissolution
  3. customwere consumed

Sources & evidence

ORD record
ord-d845599f1c7044d29f69bada8a0d5e80
Source dataset
uspto-grants-2012_11
Patent number
US08314110B2

Reaction notes

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