Diisopropylethylamine → 5-Chloro-2-[4-(3-[1,2,4]triazol-4-yl-benzylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-benzonitrile

HRID 657804Notes

Reaction equation

HRID 657804 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:20][CH2:19][C:13]3[N:14]=[CH:15][N:16]=[C:17](Cl)[C:12]=3[CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8].[N:21]1[N:22]=[CH:23][N:24]([C:26]2[CH:27]=[C:28]([CH2:32][NH2:33])[CH:29]=[CH:30][CH:31]=2)[CH:25]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:10]2[CH2:20][CH2:19][C:13]3[N:14]=[CH:15][N:16]=[C:17]([NH:33][CH2:32][C:28]4[CH:29]=[CH:30][CH:31]=[C:26]([N:24]5[CH:25]=[N:21][N:22]=[CH:23]5)[CH:27]=4)[C:12]=3[CH2:11]2)=[C:6]([CH:9]=1)[C:7]#[N:8]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 598406875-Chloro-2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrileHCID 59840698(3-(4H-1,2,4-triazol-4-yl)phenyl)methanamine

Product 1

HCID 250598075-Chloro-2-[4-(3-[1,2,4]triazol-4-yl-benzylamino)-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl]-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture of 5-chloro-2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)benzonitrile (80 mg, 0.26 mmol) and (3-(4H-1,2,4-triazol-4-yl)phenyl)methanamine (120 mg, 0.40 mmol) in acetonitrile (1 mL) and N,N-diisopropylethylamine (0.6 mL, 4 mmol) was subjected to microwave irradiation at 185° C. for 2.5 h. The reaction mixture was concentrated and purified by semi-preparative HPLC (100×20.2 mm, C18 column; 30-50% CH3CN-water [10 mM Et2NH]) to yield a light yellow solid.

Workup

  1. customirradiation at 185° C. for 2.5 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by semi-preparative HPLC (100×20.2 mm, C18 column; 30-50% CH3CN-water [10 mM Et2NH])
  4. customto yield a light yellow solid

Sources & evidence

ORD record
ord-004b780f7f6a4665a56e52a120b4d36d
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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