Diisopropylethylamine → HCID 118162164, compound

HRID 1749459Notes

Reaction equation

HRID 1749459 reaction equation
[NH2:1][C@@H:2]1[CH2:5][C@H:4]([OH:6])[C:3]1([CH3:8])[CH3:7].Cl[C:10]1[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]([S:18][CH3:19])[N:11]=1.CCN(C(C)C)C(C)C>C(O)(C)C>[OH:6][C@H:4]1[CH2:5][C@@H:2]([NH:1][C:10]2[C:15]([C:16]#[N:17])=[CH:14][N:13]=[C:12]([S:18][CH3:19])[N:11]=2)[C:3]1([CH3:8])[CH3:7]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 131141834-Chloro-2-(methylsulfanyl)pyrimidine-5-carbonitrileHCID 97300410HCID 97300410, compound

Product 1

HCID 118162164HCID 118162164, compoundYield 66.3%

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Conditions

Temperature
85 °C

Procedure

A mixture of (1S,3R)-3-amino-2,2-dimethylcyclobutanol (550 mg crude), 4-chloro-2-(methylthio)pyrimidine-5-carbonitrile (887 mg, 4.78 mmol) and DIEA (1.12 g, 8.7 mmol) in isopropanol (20 mL) was stirred at 85° C. for 3 h. After cooling to room temperature, the reaction mixture was concentrated and the residue was purified by silica gel column chromatography (0.6% MeOH in DCM) to afford the title compound (760 mg, 2.88 mmol, 66.3% yield). MS (ESI) m/z 265.1 [M+1]+.

Workup

  1. temperatureAfter cooling to room temperature
  2. concentrationthe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (0.6% MeOH in DCM)

Sources & evidence

ORD record
ord-72e7ff3294c24ec0b3b8570cc38e4001
Source dataset
uspto-grants-2015_10
Patent number
US09156798B2

Reaction notes

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