Carbon Tetrachloride → tert-Butyl 4-chloro-8-methyl-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate

HRID 45082

Reaction equation

HRID 45082 reaction equation
[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](=O)[NH:13][CH:12]=[N:11][C:10]=2[CH:9]1[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)[Cl:40]>ClCCCl>[C:1]([O:5][C:6]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([Cl:40])=[N:13][CH:12]=[N:11][C:10]=2[CH:9]1[CH3:19])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 1361587808-methyl-4-oxo-4,5,6,8-tetrahydro-3H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester

Product 1

HCID 59394669tert-Butyl 4-chloro-8-methyl-5,8-dihydropyrido[3,4-d]pyrimidine-7(6H)-carboxylate

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

A combination of 8-methyl-4-oxo-4,5,6,8-tetrahydro-3H-pyrido[3,4-d]pyrimidine-7-carboxylic acid tert-butyl ester (374 mg, 1.41 mmol), triphenylphosphine (739 mg, 2.82 mmol) and carbon tetrachloride (409 uL, 4.23 mmol) and 1,2-DCE (10 mL) are heated at 70° C. for 6 h. The solution is then concentrated in vacuo and the residue separated via FCC (5-60% EtOAc/heptane). MS (ESI) m/z 284.2 (M+H).

Workup

  1. concentrationThe solution is then concentrated in vacuo
  2. customthe residue separated via FCC (5-60% EtOAc/heptane)

Sources & evidence

ORD record
ord-42243e31106248d9ba24c74d8de6858e
Source dataset
uspto-grants-2013_09
Patent number
US08541432B2

Linked notes

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