Acetic Acid → (6-Chloro-pyrimidin-4-yl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine

HRID 469853Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH2:8])[CH:3]=1.[CH:9]1([O:14][C:15]2[CH:16]=[C:17]([CH:20]=[CH:21][C:22]=2[O:23][CH3:24])[CH:18]=O)[CH2:13][CH2:12][CH2:11][CH2:10]1.CC(O)=O>ClCCCl>[Cl:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]([NH:8][CH2:18][C:17]2[CH:20]=[CH:21][C:22]([O:23][CH3:24])=[C:15]([O:14][CH:9]3[CH2:13][CH2:12][CH2:11][CH2:10]3)[CH:16]=2)[CH:3]=1

Participants

Conditions

Temperature: 50 °C

Procedure

Sodium tiracetoxyl-borohydride (985 mg, 4.65 mmol) was added to a solution of 6-chloro-pyrimidin-4-ylamine (200 mg, 1.55 mmol) and 3-cyclopentyloxy-4-methoxy-benzaldehyde (682 mg, 3.1 mmol) in 25 ml of DCE. 1 ml of HOAc was added, and the mixture was stirred overnight at 50° C., followed by addition of 25 ml of DCE. The organic phase was washed with water, and the product was purified with column (silica gel, hexane:EtOAc 5:1) to give 64 mg of (6-chloro-pyrimidin-4-yl)-(3-cyclopentyloxy-4-methoxy-benzyl)-amine, yield 12%.

Workup

washThe organic phase was washed with water
customthe product was purified with column (silica gel, hexane:EtOAc 5:1)

Sources & evidence

ORD record: ord-cca2e489f75a472da43c44b6d4bc5fb2
Source dataset: uspto-grants-2014_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08629156B2

Reaction notes

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