Diisopropylethylamine → (S)-2-[6-(5-Chloro-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ylamino]-2-(6-methoxy-pyridin-3-yl)-ethanol

HRID 241881Notes

Reaction equation

HRID 241881 reaction equation
Cl[C:2]1[C:3]2[CH2:11][N:10]([C:12]3[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][N:13]=3)[CH2:9][CH2:8][C:4]=2[N:5]=[CH:6][N:7]=1.[NH2:19][C@@H:20]([C:23]1[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=1)[CH2:21][OH:22].C(N(CC)C(C)C)(C)C>C(#N)C>[Cl: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:19][C@@H:20]([C:23]4[CH:24]=[N:25][C:26]([O:29][CH3:30])=[CH:27][CH:28]=4)[CH2:21][OH:22])[C:3]=3[CH2:11]2)=[N:13][CH:14]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 55278315(S)-2-Amino-2-(6-methoxypyridin-3-yl)ethanolHCID 581035874-Chloro-6-(5-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine

Product 1

HCID 25032349(S)-2-[6-(5-Chloro-pyridin-2-yl)-5,6,7,8-tetrahydro-pyrido[4,3-d]pyrimidin-4-ylamino]-2-(6-methoxy-pyridin-3-yl)-ethanol

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A reaction mixture of 4-chloro-6-(5-chloropyridin-2-yl)-5,6,7,8-tetrahydropyrido[4,3-d]pyrimidine (55 mg, 0.20 mmol) and (S)-2-amino-2-(6-methoxypyridin-3-yl)ethanol (33 mg, 0.20 mmol) in acetonitrile (2 mL) and N,N-diisopropylethylamine (68 μL, 0.39 mmol) was subjected to microwave irradiation at 180° C. for 2 h. The reaction mixture was concentrated and purified by semi-prep HPLC (100×20.2 mm, C18 column; 25-50% CH3CN-water [10 mM Et2NH]) to give an off-white solid.

Workup

  1. customirradiation at 180° C. for 2 h
  2. concentrationThe reaction mixture was concentrated
  3. custompurified by semi-prep HPLC (100×20.2 mm, C18 column; 25-50% CH3CN-water [10 mM Et2NH])
  4. customto give an off-white solid

Sources & evidence

ORD record
ord-e3a1d767cde7447c850e6385cd636379
Source dataset
uspto-grants-2014_02
Patent number
US08653091B2

Reaction notes

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