Hydrochloric Acid → HCID 178433339, compound

HRID 641691Notes

Reaction equation

HRID 641691 reaction equation
[Li+].[OH-].[NH2:3][C:4]1[N:5]=[C:6]([CH3:29])[C:7]2[CH:13]=[C:12]([C:14]([O:16]CCCC)=[O:15])[C:11](=[O:21])[N:10]([C@H:22]3[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]3)[C:8]=2[N:9]=1.Cl>C1COCC1.CO.[Cl-].[Na+].O.O.CCO.C(Cl)Cl>[NH2:3][C:4]1[N:5]=[C:6]([CH3:29])[C:7]2[CH:13]=[C:12]([C:14]([OH:16])=[O:15])[C:11](=[O:21])[N:10]([C@H:22]3[CH2:27][CH2:26][C@H:25]([OH:28])[CH2:24][CH2:23]3)[C:8]=2[N:9]=1

Participants

10

Reactant 3

HCID 313Hydrochloric AcidHCID 3939Lithium HydroxideHCID 178450628HCID 178450628, compound

Product 1

HCID 178433339HCID 178433339, compoundYield 115.5%

Reagents, catalysts & solvents 6

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent2×HCID 6344DichloromethaneSolventHCID 8028TetrahydrofuranSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

A 1M solution of LiOH in H2O (0.81 mL, 0.81 mmol) was added to a suspension of butyl 2-amino-8-(trans-4-hydroxycyclohexyl)-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylate (0.25 g, 0.68 mmol) in THF (7 mL) and MeOH (2 mL). After 2.5 h, DCM, EtOH, water, brine, celite and 0.7 mL of 1 M HCl were added. The mixture was filtered. The organic layer was separated and concentrated by rotary evaporation to afford 0.25 g of 2-amino-8-(trans-4-hydroxycyclohexyl)-4-methyl-7-oxo-7,8-dihydropyrido[2,3-d]pyrimidine-6-carboxylic acid.

Workup

  1. filtrationThe mixture was filtered
  2. customThe organic layer was separated
  3. concentrationconcentrated by rotary evaporation

Sources & evidence

ORD record
ord-b79a4e62d925490683b0da1f6e3c08ae
Source dataset
uspto-grants-2010_04
Patent number
US07696213B2

Reaction notes

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