Diisopropylethylamine → [6-(5-Methyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yl]-[(R)-1-(2-methyl-pyrimidin-5-yl)-ethyl]-amine

HRID 241884Notes

Reaction equation

HRID 241884 reaction equation
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:17]=[CH:16][C:15]([CH3:18])=[CH:14][N:13]=3)[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[CH3:19][C:20]1[N:25]=[CH:24][C:23]([C@H:26]([NH2:28])[CH3:27])=[CH:22][N:21]=1.C(N(CC)C(C)C)(C)C>C(#N)C>[CH3:18][C:15]1[CH:16]=[CH:17][C:12]([N:10]2[CH2:9][CH2:8][C:4]3[N:5]=[CH:6][N:7]=[C:2]([NH:28][C@@H:26]([C:23]4[CH:22]=[N:21][C:20]([CH3:19])=[N:25][CH:24]=4)[CH3:27])[C:3]=3[CH2:11]2)=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 55281681(R)-1-(2-Methyl-5-pyrimidinyl)ethanamineHCID 593464574-Chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine

Product 1

HCID 24995216[6-(5-Methyl-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-yl]-[(R)-1-(2-methyl-pyrimidin-5-yl)-ethyl]-amine

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture of 4-chloro-5,6,7,8-tetrahydro-6-(5-methylpyridin-2-yl)pyrido[4,3-d]pyrimidine (120 mg, 0.46 mmol) and (R)-1-(2-methylpyrimidin-5-yl)ethanamine (120 mg, 0.87 mmol) in acetonitrile (1 mL) and N,N-diisopropylethylamine (500 μL, 3 mmol) was subjected to microwave irradiation at 185° C. for 3.5 h. The reaction mixture was concentrated and the residue was purified by semi-prep HPLC (100×20.2 mm, C18 column; 30-55% CH3CN-water [10 mM Et2NH]) to give a light color solid. LC-MS: 362.4 [M+H]+;

Workup

  1. customirradiation at 185° C. for 3.5 h
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by semi-prep HPLC (100×20.2 mm, C18 column; 30-55% CH3CN-water [10 mM Et2NH])
  4. customto give a light color solid

Sources & evidence

ORD record
ord-a174ea33c4214ffba3fd6e0825785065
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Reaction notes

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