Diisopropylethylamine → HCID 25253280, compound

HRID 2063485Notes

Reaction equation

HRID 2063485 reaction equation
Cl.[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][C:8]2[C:9]([CH3:19])=[N:10][CH:11]=[N:12][C:13]=2[C@H:14]2[CH2:18][CH2:17][CH2:16][NH:15]2)=[CH:5][CH:4]=1.C(N(CC)C(C)C)(C)C.[N:31]([C:34]1[C:35]([CH3:40])=[N:36][O:37][C:38]=1[CH3:39])=[C:32]=[O:33]>ClCCl>[Cl:2][C:3]1[CH:21]=[CH:20][C:6]([CH2:7][C:8]2[C:13]([C@H:14]3[CH2:18][CH2:17][CH2:16][N:15]3[C:32]([NH:31][C:34]3[C:35]([CH3:40])=[N:36][O:37][C:38]=3[CH3:39])=[O:33])=[N:12][CH:11]=[N:10][C:9]=2[CH3:19])=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 27362663,5-Dimethylisoxazole-4-isocyanateHCID 68812424HCID 68812424, compound

Product 1

HCID 25253280HCID 25253280, compoundYield 28.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

(R)-5-(4-chlorobenzyl)-4-methyl-6-(pyrrolidin-2-yl)pyrimidine hydrochloride (30 mg, 0.066 mmol) and N,N-diisopropylethylamine (0.041 mL) were dissolved in dichloromethane (2 mL). 4-isocyanato-3,5-dimethylisoxazole (15 mg, 0.11 mmol) was added while stirring. The reaction mixture was stirred for 16 h then evaporated to dryness. Purification by semi-preparative HPLC afforded the desired product (7.9 mg, 27.8%).

Workup

  1. stirringThe reaction mixture was stirred for 16 h
  2. customthen evaporated to dryness
  3. customPurification by semi-preparative HPLC

Sources & evidence

ORD record
ord-c5c61a6c7cdf4ca59ac89a8ed3689e9d
Source dataset
uspto-grants-2012_10
Patent number
US08288371B2

Reaction notes

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