2-Chloro-4-methylpyrimidine → HCID 136188919, compound

HRID 1961803Notes

Reaction equation

HRID 1961803 reaction equation
[Cl:1][C:2]1[C:11]([NH:12][C:13]([O:15][CH2:16][CH:17]=[CH2:18])=[O:14])=[CH:10][CH:9]=[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:1][C:2]1[C:3](/[C:4](/[OH:6])=[CH:26]\[C:24]2[CH:23]=[CH:22][N:21]=[C:20]([Cl:19])[N:25]=2)=[CH:8][CH:9]=[CH:10][C:11]=1[NH:12][C:13](=[O:14])[O:15][CH2:16][CH:17]=[CH2:18]

Participants

3

Reactant 2

HCID 116296072-Chloro-4-methylpyrimidineHCID 57989809HCID 57989809, compound

Product 1

HCID 136188919HCID 136188919, compoundYield 79.6%

Procedure

Following a procedure analogous to the procedure described in Intermediate 5, Step B using methyl 2-chloro-3-{[(2-propen-1-yloxy)carbonyl]amino}benzoate (30 g, 0.11 mol) and 2-chloro-4-methylpyrimidine (15.8 g, 0.12 mol) the title compound of Step B was prepared (29 g, 79.6% yield). 1H NMR (400 MHz, CDCl3) δ ppm 13.52-13.58 (br, 0.9H), 8.41-8.42 (m, 1H), 8.22-8.27 (m, 1H), 7.28-7.35 (m, 2.2H), 7.21-7.24 (m, 1.2H), 6.85-6.88 (m, 1H), 5.91-6.02 (m, 1H), 5.73 (s, 1H), 5.23-5.40 (m, 2H), 4.66-4.70 (m, 2H).

Sources & evidence

ORD record
ord-56470a64514f49e986d60dbdca7cc5ef
Source dataset
uspto-grants-2013_04
Patent number
US08415345B2

Reaction notes

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