1,4-Dioxane → (S)-1-(1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-3-pyrimidin-4-yl-urea

HRID 40514

Reaction equation

HRID 40514 reaction equation
C1CCN2C(=NCCC2)CC1.[NH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][N:14]=1.[CH2:19]([O:21][C:22]1[CH:41]=[CH:40][C:25]([O:26][CH:27]2[CH2:30][N:29]([C:31]3[CH:36]=[CH:35][C:34]([C@@H:37]([NH2:39])[CH3:38])=[CH:33][CH:32]=3)[CH2:28]2)=[CH:24][CH:23]=1)[CH3:20].[O:42]1CCOC[CH2:43]1>>[CH2:19]([O:21][C:22]1[CH:41]=[CH:40][C:25]([O:26][CH:27]2[CH2:28][N:29]([C:31]3[CH:36]=[CH:35][C:34]([C@@H:37]([NH:39][C:43]([NH:12][C:13]4[CH:18]=[CH:17][N:16]=[CH:15][N:14]=4)=[O:42])[CH3:38])=[CH:33][CH:32]=3)[CH2:30]2)=[CH:24][CH:23]=1)[CH3:20]

Participants

5

Reactant 4

HCID 312751,4-Dioxane2×HCID 689584-AminopyrimidineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 86689010(S)-1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine

Product 1

HCID 71616306(S)-1-(1-{4-[3-(4-Ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethyl)-3-pyrimidin-4-yl-urea

Procedure

0.03 mL (0.20 mmol) DBU and 0.033 g (0.20 mmol) CDT are added to 0.010 g (0.10 mmol) 4-aminopyrimidine in 1.0 mL 1,4-dioxane. The mixture is stirred for 5 min at rt followed by addition of 0.048 g (0.092 mmol) (S)-1-{4-[3-(4-ethoxy-phenoxy)-azetidin-1-yl]-phenyl}-ethylamine (X.1) in 1.0 mL 1,4-dioxane. The mixture is stirred for 12 h at rt and subsequently concentrated in vacuo. The residue is purified by HPLC (XBridge, ACN/water (+0.1% NH4OH)) to yield the desired product.

Workup

  1. stirringThe mixture is stirred for 12 h at rt
  2. concentrationsubsequently concentrated in vacuo
  3. customThe residue is purified by HPLC (XBridge, ACN/water (+0.1% NH4OH))

Sources & evidence

ORD record
ord-30a23b06abe14314b3991ac4d9ca0352
Source dataset
uspto-grants-2013_09
Patent number
US08530461B2

Linked notes

Loading…