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

HRID 1671122Notes

Reaction equation

HRID 1671122 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8]C(C2C=C(NC(=O)OCC=C)C=CC=2)=O)[CH:5]=[CH:4][N:3]=1.[F:24][C:25]1[C:34]([NH:35][C:36]([O:38][CH2:39][CH:40]=[CH2:41])=[O:37])=[CH:33][CH:32]=[C:31]([F:42])[C:26]=1[C:27]([O:29]C)=O.ClC1N=C(C)C=CN=1>>[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][C:27]([C:26]2[C:25]([F:24])=[C:34]([NH:35][C:36](=[O:37])[O:38][CH2:39][CH:40]=[CH2:41])[CH:33]=[CH:32][C:31]=2[F:42])=[O:29])[CH:5]=[CH:4][N:3]=1

Participants

4

Reactant 3

HCID 116296072-Chloro-4-methylpyrimidineHCID 57989916HCID 57989916, compoundHCID 579899812-Propen-1-yl {3-[(2-chloro-4-pyrimidinyl)acetyl]phenyl}carbamate

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-be42cc95d7c84075a128c20ef06d6d4c
Source dataset
uspto-grants-2011_08
Patent number
US07994185B2

Reaction notes

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