Hydrochloric Acid → HCID 57531599, compound

HRID 1091935Notes

Reaction equation

[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[C:5]([CH2:9][CH3:10])[C:4]=1[C:11]1[N:16]=[C:15]([C:17]#[N:18])[C:14]([CH2:19][N:20]([CH3:31])[C@@H:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24][CH2:23][CH2:22]2)=[C:13]([CH3:32])[N:12]=1)[CH3:2].CC(C[AlH]CC(C)C)C.Cl.[OH-].[Na+]>C1(C)C=CC=CC=1.CCOC(C)=O>[NH2:18][CH2:17][C:15]1[C:14]([CH2:19][N:20]([CH3:31])[C@@H:21]2[C:30]3[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=3)[CH2:24][CH2:23][CH2:22]2)=[C:13]([CH3:32])[N:12]=[C:11]([C:4]2[C:3]([CH2:1][CH3:2])=[CH:8][CH:7]=[CH:6][C:5]=2[CH2:9][CH3:10])[N:16]=1

Participants

Conditions

Temperature: 0 °C

Procedure

To a flask containing 2-(2,6-diethylphenyl)-6-methyl-5-({methyl[(1S)-1,2,3,4-tetrahydronaphthalen-1-yl]amino}methyl)pyrimidine-4-carbonitrile (50 mg, 0.118 mmol) in toluene (5.0 mL) is cooled to 0° C. using an ice bath. DIBAL (0.354 mL of a 1.5 M solution in toluene, 3.0 eq., 0.53 mmol) is then added and the reaction is allowed to proceed for 3 h warming to room temperature. HCl (1.0 M 1.0 mL) is added and allowed to stir for 10 min, followed by basification with NaOH (5N). EtOAc (20 mL) is added and the organic layer is washed with NaHCO3 (10%, 100 mL), brine (100 mL) and dried over Na2SO4. SiO2 plate chromatography eluting with 20:1 CHCl3:MeOH affords the title compound as a white foam. [mass expected (428.61); mass found (428.38)].

Workup

temperaturewarming to room temperature
washthe organic layer is washed with NaHCO3 (10%, 100 mL), brine (100 mL)
dry with materialdried over Na2SO4
washSiO2 plate chromatography eluting with 20:1 CHCl3

Sources & evidence

ORD record: ord-b94bd695b00e462ba099a62fdc7558b2
Source dataset: uspto-grants-2012_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08129395B2

Reaction notes

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