Hydrochloric Acid → HCID 57531599, compound

HRID 1455753Notes

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-89688cbe27954df49e7b5384045faa37
Source dataset: uspto-grants-2009_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07482350B2

Reaction notes

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