Allylamine → HCID 21090184, compound

HRID 1713243Notes

Reaction equation

HRID 1713243 reaction equation
[Cl:1][C:2]1[C:7](=[O:8])[N:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:12]([O:14][CH3:15])=[O:13])[C:5](S(C)(=O)=O)=[N:4][C:3]=1[O:24][CH2:25][C:26]1[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=1[F:33].[CH2:34]([NH2:37])[CH:35]=[CH2:36].C(OCC)(=O)C>CN(C1C=CN=CC=1)C.O1CCOCC1>[CH2:34]([NH:37][C:5]1[N:6]([C:9]2[CH:10]=[C:11]([CH:16]=[CH:17][C:18]=2[CH3:19])[C:12]([O:14][CH3:15])=[O:13])[C:7](=[O:8])[C:2]([Cl:1])=[C:3]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][C:29]([F:32])=[CH:28][C:27]=2[F:33])[N:4]=1)[CH:35]=[CH2:36]

Participants

6

Reactant 3

HCID 7853AllylamineHCID 8857Ethyl AcetateHCID 21090199HCID 21090199, compound

Product 1

HCID 21090184HCID 21090184, compoundYield 41%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 312751,4-DioxaneSolvent

Procedure

A mixture of methyl 3-[5-chloro-4-[(2,4-difluorobenzyl)oxy]-2-(methylsulfonyl)-6-oxopyrimidin-1(6H)-yl]-4-methylbenzoate (from Step 1) (3.02 g, 6.05 mmol), allyl amine (0.55 mL, 7.26 mmol), and DMAP (0.07 g, 0.61 mmol) in dioxane (8 mL) was stirred at ambient temperature overnight. Observed product and impurity (1:1 ratio). Added ethyl acetate (4 mL), cooled (0° C.) the reaction mixture, filtered the precipitate, and dried in vacuo to give the product as a white solid (1.17 g, 41%). 1H NMR (CD3OD/400 MHz) δ8.08 (m, 1H), 7.82 (s, 1H), 7.57 (m, 2H), 7.00 (t, 2H, J=8.8 Hz), 5.80 (m, 1H), 5.51 (m, 2H), 5.07 (m, 2H), 4.56 (s, 1H), 3.93 (m, 1H), 3.89 (s, 3H), 3.65 (s, 3H). ESHRMS m/z 476.1184 (M+H calculated for C23H21ClF2N3O4 requires 476.1183).

Workup

  1. filtrationfiltered the precipitate
  2. customdried in vacuo

Sources & evidence

ORD record
ord-3f1b9f8de56f49dfa558542067097a11
Source dataset
uspto-grants-2010_09
Patent number
US07795271B2

Reaction notes

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