2-Chloro-4-methylpyrimidine → 2-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2,4-difluorophenyl}carbamate

HRID 590224Notes

Reaction equation

HRID 590224 reaction equation
[F:1][C:2]1[C:11]([NH:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])=[CH:10][CH:9]=[C:8]([F:19])[C:3]=1[C:4]([O:6]C)=O.[Cl:20][C:21]1[N:26]=[C:25]([CH3:27])[CH:24]=[CH:23][N:22]=1>>[Cl:20][C:21]1[N:26]=[C:25]([CH2:27][C:4]([C:3]2[C:2]([F:1])=[C:11]([NH:12][C:13](=[O:14])[O:15][CH2:16][CH:17]=[CH2:18])[CH:10]=[CH:9][C:8]=2[F:19])=[O:6])[CH:24]=[CH:23][N:22]=1

Participants

3

Reactant 2

HCID 116296072-Chloro-4-methylpyrimidineHCID 57989916HCID 57989916, compound

Product 1

HCID 579899062-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-2,4-difluorophenyl}carbamateYield 60.2%

Procedure

Following a procedure analogous to the procedure described in Intermediate 11 using methyl 2,6-difluoro-3-{[(2-propen-1-yloxy)carbonyl]amino}benzoate (80 g, 295 mmol) and 2-chloro-4-methylpyrimidine (41.6 g, 324 mmol) the title compound of Step E was obtained (65 g, 60.2% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 9.49-9.60 (m, 1H), 8.72-8.77 (m, 0.3H), 8.58-8.64 (m, 0.6H), 7.57-7.83 (m, 2H), 7.15-7.25 (m, 1H), 5.89-6.01 (m, 1H), 5.75-5.82 (m, 0.6H), 5.20-5.40 (m, 2H), 4.55-4.62 (m, 2H), m/z (ES+): 368 [M+H]+.

Sources & evidence

ORD record
ord-2c646940fa9249d1be4d39095f4920c7
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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