Triethylamine → tert-butyl 4-chloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

HRID 335147Notes

Reaction equation

HRID 335147 reaction equation
C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl:20]N1C(=O)CCC1=O.O[C:29]1[C:30]2[CH2:38][N:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:36][CH2:35][C:31]=2[N:32]=[CH:33][N:34]=1.C(N(CC)CC)C>O1CCOCC1>[Cl:20][C:29]1[C:30]2[CH2:38][N:37]([C:39]([O:41][C:42]([CH3:45])([CH3:44])[CH3:43])=[O:40])[CH2:36][CH2:35][C:31]=2[N:32]=[CH:33][N:34]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 31398ChlorosuccinimideHCID 178451656HCID 178451656, compound

Product 1

HCID 56924365tert-butyl 4-chloro-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture of PPh3 (81.4 g, 310 mmol) and N-chlorosuccinimide (41.4 g, 310 mmol) in dioxane (850 mL) was stirred at ambient temperature for 30 minutes. To this suspension was added tert-butyl 4-hydroxy-7,8-dihydropyrido[4,3-d]pyrimidine-6(5H)-carboxylate and the mixture stirred at 50° C. for 18 hours. The mixture was subsequently treated with triethylamine (25 mL, 183 mmol) and the resulting brown solution concentrated. The black oil was dry packed onto silica gel and purified by chromatography eluting with 15-20% EtOAc/Hexanes to give the title compound as a yellow gum.

Workup

  1. stirringthe mixture stirred at 50° C. for 18 hours
  2. concentrationthe resulting brown solution concentrated
  3. customThe black oil was dry
  4. custompurified by chromatography
  5. washeluting with 15-20% EtOAc/Hexanes

Sources & evidence

ORD record
ord-d291644f57664f8586d2f814489a3fb0
Source dataset
uspto-grants-2014_11
Patent number
US08883828B2

Reaction notes

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