Diisopropylethylamine → 2-{4-[(5-Cyclopropyl-pyridin-2-ylmethyl)-amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-5-methyl-benzonitrile

HRID 657796Notes

Reaction equation

HRID 657796 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.[CH:21]1([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][NH2:31])=[N:28][CH:29]=2)[CH2:23][CH2:22]1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH:21]1([C:24]2[CH:25]=[CH:26][C:27]([CH2:30][NH:31][C:2]3[C:3]4[CH2:11][N:10]([C:12]5[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=5[C:14]#[N:15])[CH2:9][CH2:8][C:4]=4[N:5]=[CH:6][N:7]=3)=[N:28][CH:29]=2)[CH2:23][CH2:22]1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 55283832(5-Cyclopropylpyridin-2-yl)methanamineHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Product 1

HCID 250629462-{4-[(5-Cyclopropyl-pyridin-2-ylmethyl)-amino]-7,8-dihydro-5H-pyrido[4,3-d]pyrimidin-6-yl}-5-methyl-benzonitrile

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture of 2-(4-chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile (150 mg, 0.53 mmol) and (5-cyclopropylpyridin-2-yl)methanamine (115 mg, 0.78 mmol) in acetonitrile (2 mL) and N,N-diisopropylethylamine (0.14 mL, 0.78 mmol) was subjected to microwave irradiation at 180° C. for 2 h. The mixture was concentrated and the residue was purified by preparative HPLC (100×20.2 mm, C18 column; 50-70% CH3CN-water [10 mM Et2NH]) to yield an off-white foam.

Workup

  1. customirradiation at 180° C. for 2 h
  2. concentrationThe mixture was concentrated
  3. customthe residue was purified by preparative HPLC (100×20.2 mm, C18 column; 50-70% CH3CN-water [10 mM Et2NH])
  4. customto yield an off-white foam

Sources & evidence

ORD record
ord-c9eb6f47d56b4d4a9c0ceac944190a27
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Reaction notes

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