Aluminium lithium hydride → 2-(4-((2-(3-Chlorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)benzyl)-3-hydroxypropanamide

HRID 1508850Notes

Reaction equation

HRID 1508850 reaction equation
[NH2:1][C:2](=[O:34])[CH:3]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[C:19]3[CH2:33][CH2:32][CH2:31][C:20]=3[N:21]=[C:22]([C:24]3[CH:29]=[CH:28][CH:27]=[C:26]([Cl:30])[CH:25]=3)[N:23]=2)=[CH:13][CH:12]=1)[C:4](OC(C)C)=[O:5].[H-].[Al+3].[Li+].[H-].[H-].[H-]>C1COCC1>[Cl:30][C:26]1[CH:25]=[C:24]([C:22]2[N:23]=[C:18]([NH:17][C:14]3[CH:13]=[CH:12][C:11]([CH2:10][CH:3]([CH2:4][OH:5])[C:2]([NH2:1])=[O:34])=[CH:16][CH:15]=3)[C:19]3[CH2:33][CH2:32][CH2:31][C:20]=3[N:21]=2)[CH:29]=[CH:28][CH:27]=1

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 90112914isopropyl 3-amino-2-(4-((2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)benzyl)-3-oxopropanoate

Product 1

HCID 901095722-(4-((2-(3-Chlorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)benzyl)-3-hydroxypropanamideYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of isopropyl 3-amino-2-(4-((2-(3-chlorophenyl)-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)amino)benzyl)-3-oxopropanoate (0.090 g, 0.19 mmol) in THF (5 mL) was added lithium aluminum hydride (1.0 M, 0.38 mL, 0.38 mmol). The mixture stirred at 0° C. for 2 h. The mixture was quenched with water and sodium hydroxide (2M) and then extracted with ethyl acetate. The organic layer were dried over anhydrous sodium sulfate, filtered, and the filtrate was concentrated. The residue was purified by column chromatography (silica, dichloromethane/methanol) to afford the title compound (0.020 g, 25%) as a white solid. MW=422.91. 1H NMR (DMSO-d6, 500 MHz) δ 8.77 (s, 1H), 8.30-8.21 (m, 2H), 7.70 (d, J=8.5 Hz, 2H), 7.55-7.49 (m, 2H), 7.23 (s, 1H), 7.18 (d, J=8.0 Hz, 2H), 6.73 (s, 1H), 4.67 (t, J=5.5 Hz, 1H), 3.59-3.52 (m, 1H), 3.43-3.36 (m, 1H), 2.94-2.84 (m, 4H), 2.79-2.56 (m, 3H), 2.10 (quin, J=7.5 Hz, 2H); APCI MS m/z 423 [M+H]+.

Workup

  1. customThe mixture was quenched with water and sodium hydroxide (2M)
  2. extractionextracted with ethyl acetate
  3. dry with materialThe organic layer were dried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationthe filtrate was concentrated
  6. customThe residue was purified by column chromatography (silica, dichloromethane/methanol)

Sources & evidence

ORD record
ord-0c1a8650c31f496a94685ccfb4d8f824
Source dataset
uspto-grants-2015_12
Patent number
US09221843B2

Reaction notes

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