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

HRID 657809

Reaction equation

HRID 657809 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]([C:24]1[N:29]=[CH:28][C:27]([CH2:30][NH2:31])=[CH:26][N:25]=1)([CH3:23])[CH3:22].C(N(CC)C(C)C)(C)C>C(#N)C>[CH:21]([C:24]1[N:29]=[CH:28][C:27]([CH2:30][NH:31][C:2]2[C:3]3[CH2:11][N:10]([C:12]4[CH:19]=[CH:18][C:17]([CH3:20])=[CH:16][C:13]=4[C:14]#[N:15])[CH2:9][CH2:8][C:4]=3[N:5]=[CH:6][N:7]=2)=[CH:26][N:25]=1)([CH3:23])[CH3:22]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 59840686(2-Isopropylpyrimidin-5-YL)methanamineHCID 598406882-(4-Chloro-7,8-dihydropyrido[4,3-d]pyrimidin-6(5H)-yl)-5-methylbenzonitrile

Product 1

HCID 250600632-{4-[(2-Isopropyl-pyrimidin-5-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 (80 mg, 0.28 mmol) and (2-isopropylpyrimidin-5-yl)methanamine (60 mg, 0.40 mmol) (prepared similarly according to the method for Intermediate 13) in acetonitrile (1 mL) and N,N-diisopropylethylamine (0.3 mL, 2 mmol) was subjected to microwave irradiation at 185° C. for 3 h. The reaction mixture was concentrated and purified by semi-preparative HPLC (100×20.2 mm, C18 column; 40-60% CH3CN-water [10 mM Et2NH]) to yield a light yellow solid.

Workup

  1. customprepared similarly
  2. customirradiation at 185° C. for 3 h
  3. concentrationThe reaction mixture was concentrated
  4. custompurified by semi-preparative HPLC (100×20.2 mm, C18 column; 40-60% CH3CN-water [10 mM Et2NH])
  5. customto yield a light yellow solid

Sources & evidence

ORD record
ord-e9345327af86456db804ca518bd14b9d
Source dataset
uspto-grants-2011_12
Patent number
US08076345B2

Linked notes

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