4-(Difluoromethoxy)aniline → 7-Benzyl-N-(4-(difluoromethoxy)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amine

HRID 971209Notes

Reaction equation

HRID 971209 reaction equation
[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14](Cl)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[F:19][CH:20]([F:29])[O:21][C:22]1[CH:27]=[CH:26][C:25]([NH2:28])=[CH:24][CH:23]=1>O1CCOCC1.C(OCC)C>[CH2:1]([N:8]1[CH2:17][CH2:16][C:15]2[C:14]([NH:28][C:25]3[CH:26]=[CH:27][C:22]([O:21][CH:20]([F:19])[F:29])=[CH:23][CH:24]=3)=[N:13][CH:12]=[N:11][C:10]=2[CH2:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 7373634-(Difluoromethoxy)anilineHCID 219588387-Benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine

Product 1

HCID 590215487-Benzyl-N-(4-(difluoromethoxy)phenyl)-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidin-4-amineYield 81%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 312751,4-DioxaneSolvent

Procedure

A mixture of 7-benzyl-4-chloro-5,6,7,8-tetrahydropyrido[3,4-d]pyrimidine prepared as described in Example 1.B. (1.09 g, 4.21 mmol) and 4-(difluoromethoxy)benzenamine (1.34 g, 8.42 mmol) in 1,4-dioxane (15 mL) was heated in a sealed tube at 100° C. for 16 h. The dark slurry was cooled to r.t. and diluted with diethyl ether. The solid was collected by flitration and triturated with ethyl acetate:hexane (1:9) and dried to give a tan solid (1.3 g, 81%) which was used directly.

Workup

  1. customprepared
  2. customThe solid was collected by flitration
  3. customtriturated with ethyl acetate:hexane (1:9)
  4. customdried

Sources & evidence

ORD record
ord-a5a59b67348e45a3a11825f626711543
Source dataset
uspto-grants-2007_12
Patent number
US07312330B2

Reaction notes

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