3-Chloro-4-fluoroaniline → (3-Chloro-4-fluoro-phenyl)-(6-methyl-pyrido[3,4-d]pyrimidin-4-yl)-amine Hydrochloride

HRID 1937406Notes

Reaction equation

HRID 1937406 reaction equation
[CH3:1][C:2]1[N:12]=[CH:11][C:5]2[N:6]=[CH:7][NH:8][C:9](=O)[C:4]=2[CH:3]=1.[Cl:13][C:14]1[CH:15]=[C:16]([CH:18]=[CH:19][C:20]=1[F:21])[NH2:17]>>[ClH:13].[Cl:13][C:14]1[CH:15]=[C:16]([NH:17][C:9]2[C:4]3[CH:3]=[C:2]([CH3:1])[N:12]=[CH:11][C:5]=3[N:6]=[CH:7][N:8]=2)[CH:18]=[CH:19][C:20]=1[F:21]

Participants

3

Reactant 2

HCID 97083-Chloro-4-fluoroanilineHCID 1359920016Methyl-pyrido[3,4-d]pyrimid-4one

Product 1

HCID 22460828(3-Chloro-4-fluoro-phenyl)-(6-methyl-pyrido[3,4-d]pyrimidin-4-yl)-amine Hydrochloride

Procedure

This product was prepared from 6-methyl-pyrido[3,4-d]pyrimid-4-one (1.0 eq.) and 3-chloro-4-fluoro-aniline (1.5 eq.) according to the procedure described for Example 61. The crude product from the filtrate was chromatographed on silica using a gradient of 0% to 10% methanol/methylene chloride to afford the free base of the title product which was converted to the title product as described for Example 60 (47%; M.P. 251-258° C.; LC-MS: 289, 291 (MH+); anal. RP-HPLC:4.18 min.).

Workup

  1. customThe crude product from the filtrate was chromatographed on silica using a gradient of 0% to 10% methanol/methylene chloride

Sources & evidence

ORD record
ord-9e3c733910094cbfadea215cd9ed5156
Source dataset
uspto-grants-2002_05
Patent number
US06395733B1

Reaction notes

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