2-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile → HCID 69177701, compound

HRID 657807Notes

Reaction equation

HRID 657807 reaction equation
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=3[C:14]#[N:15])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[Si:21]([O:28][CH2:29][C@H:30]([C:32]1[CH:33]=[N:34][C:35]([O:38][CH3:39])=[N:36][CH:37]=1)[NH2:31])([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]>C(#N)C.C(N(CC)C(C)C)(C)C>[Si:21]([O:28][CH2:29][C@@H:30]([NH:31][C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=3[C:14]#[N:15])[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1)[C:32]1[CH:37]=[N:36][C:35]([O:38][CH3:39])=[N:34][CH:33]=1)([C:24]([CH3:27])([CH3:26])[CH3:25])([CH3:23])[CH3:22]

Participants

5

Reactant 2

HCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrileHCID 68420239HCID 68420239, compound

Product 1

HCID 69177701HCID 69177701, compound

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 81531DiisopropylethylamineSolvent

Procedure

A reaction mixture of 2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile (500 mg, 1.76 mmol) and (S)-2-(tert-butyldimethylsilyloxy)-1-(2-methoxypyrimidin-5-yl)ethanamine (800 mg, 2.82 mmol) in acetonitrile (10 mL) and N,N-diisopropylethylamine (1 mL) was subjected to microwave irradiation at 185° C. for 3 h. The reaction mixture was concentrated and the residue was purified by silica-gel column to afford a light yellow solid.

Workup

  1. customirradiation at 185° C. for 3 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica-gel column
  4. customto afford a light yellow solid

Sources & evidence

ORD record
ord-765a23c3114a4b50b678c7bc44a9ebd8
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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