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

HRID 590238Notes

Reaction equation

HRID 590238 reaction equation
[F:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])=[CH:8][C:3]=1[C:4]([O:6]C)=O.[Cl:19][C:20]1[N:25]=[C:24]([CH3:26])[CH:23]=[CH:22][N:21]=1>>[Cl:19][C:20]1[N:25]=[C:24]([CH2:26][C:4]([C:3]2[CH:8]=[C:9]([NH:12][C:13](=[O:14])[O:15][CH2:16][CH:17]=[CH2:18])[CH:10]=[CH:11][C:2]=2[F:1])=[O:6])[CH:23]=[CH:22][N:21]=1

Participants

3

Reactant 2

HCID 116296072-Chloro-4-methylpyrimidineHCID 57990057Methyl 2-fluoro-5-{[(2-propen-1-yloxy)carbonyl]amino}benzoate

Product 1

HCID 579897622-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]-4-fluorophenyl}carbamateYield 69.9%

Procedure

Using multiple interations of a procedure analogous to the procedure described in Intermediate 11 using methyl 2-fluoro-5-{[(2-propen-1-yloxy)carbonyl]amino}benzoate (104 g, 411 mmol) and 2-chloro-4-methylpyrimidine (59 g, 493 mmol), the title compound of Step B was obtained (100 g, 69.9% yield). 1H NMR (400 MHz, CDCl3) δ ppm 13.67-13.75 (br, 1H), 8.50-8.53 (m, 0.3H), 8.31-8.38 (m, 1H), 7.50-7.82 (m, 2.6H), 6.56-7.20 (m, 3.5H), 6.20-6.25 (m, 1H), 5.82-6.01 (1.3H), 5.20-5.40 (m, 2.6H), 4.50-4.61 (m, 2.6H), 4.31-4.41 (m, 0.9H).

Sources & evidence

ORD record
ord-4dafab52f417411db7aaa6ea0907bb76
Source dataset
uspto-grants-2016_01
Patent number
US09233956B2

Reaction notes

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