2,3-Dichloropyridine → 7-(3-Chloropyridin-2-yl)-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidin-4-amine

HRID 971238Notes

Reaction equation

HRID 971238 reaction equation
C(N(C(C)C)CC)(C)C.[F:10][C:11]([F:33])([F:32])[C:12]1[CH:17]=[CH:16][C:15]([NH:18][C:19]2[C:20]3[CH2:31][CH2:30][NH:29][CH2:28][C:21]=3[N:22]=[C:23]([CH2:25][O:26][CH3:27])[N:24]=2)=[CH:14][CH:13]=1.Cl[C:35]1[C:40]([Cl:41])=[CH:39][CH:38]=[CH:37][N:36]=1>O1CCOCC1.C(N(CC)C(=O)C)C>[Cl:41][C:40]1[C:35]([N:29]2[CH2:30][CH2:31][C:20]3[C:19]([NH:18][C:15]4[CH:16]=[CH:17][C:12]([C:11]([F:10])([F:32])[F:33])=[CH:13][CH:14]=4)=[N:24][C:23]([CH2:25][O:26][CH3:27])=[N:22][C:21]=3[CH2:28]2)=[N:36][CH:37]=[CH:38][CH:39]=1

Participants

6

Reactant 3

HCID 169882,3-DichloropyridineHCID 81531DiisopropylethylamineHCID 59021578N-(4-(Trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidin-4-amine

Product 1

HCID 590214637-(3-Chloropyridin-2-yl)-N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidin-4-amineYield 11.9%

Reagents, catalysts & solvents 2

HCID 12703N,N-DiethylacetamideSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of diisopropylethylamine (490 mg, 3.8 mmol), N-(4-(trifluoromethyl)phenyl)-5,6,7,8-tetrahydro-2-(methoxymethyl)pyrido[3,4-d]pyrimidin-4-amine (˜1.9 mmol) and 2,3-dichloropyridine (562 mg, 3.8 mmol) in dioxane (5 mL) and N,N-diethylacetamide (1.0 mL) was irradiated in microwave at 180° C. for 10 h. Solvent was removed in vacuo and the residue was purified by column chromatography. The product was obtained as a beige solid (102 mg).

Workup

  1. customwas irradiated in microwave at 180° C. for 10 h
  2. customSolvent was removed in vacuo
  3. customthe residue was purified by column chromatography

Sources & evidence

ORD record
ord-e6f62286e0ec4bac9063ac6cdbfb86be
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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