Methyl 4-methoxyacetoacetate → HCID 67072511, compound

HRID 1242436Notes

Reaction equation

[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([OH:15])=[CH:11][C:10]=1[CH3:16])([CH3:7])[CH3:6])[CH3:2].Cl[CH2:19][C:20]1[C:21]([CH2:36][O:37][CH3:38])=[N:22][C:23]([C:26]2[CH:31]=[CH:30][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:28][CH:27]=2)=[N:24][CH:25]=1.COCC(=O)CC(OC)=O.Cl.FC(F)(F)C1N=CC(C2C(C(N)=N)=CC=CC=2)=CC=1>>[CH2:1]([O:3][C:4](=[O:17])[C:5]([O:8][C:9]1[CH:14]=[CH:13][C:12]([O:15][CH2:19][C:20]2[C:21]([CH2:36][O:37][CH3:38])=[N:22][C:23]([C:26]3[CH:27]=[CH:28][C:29]([C:32]([F:35])([F:34])[F:33])=[CH:30][CH:31]=3)=[N:24][CH:25]=2)=[CH:11][C:10]=1[CH3:16])([CH3:6])[CH3:7])[CH3:2]

Participants

Reactant 4

HCID 123500Methyl 4-methoxyacetoacetate

HCID 16756990Ethyl 2-(4-hydroxy-2-methylphenoxy)-2-methylpropanoate

HCID 21935614HCID 21935614, compound

HCID 21935954HCID 21935954, compound

Product 1

HCID 67072511HCID 67072511, compound

Procedure

In analogy to the procedures described in example 101A], 2-(4-hydroxy-2-methyl-phenoxy)-2-methyl-propionic acid ethyl ester (described in WO 02/092590) was reacted with 5-chloromethyl-4-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidine (prepared from methyl 4-methoxyacetoacetate and 6-(trifluoromethyl)pyridine-3-benzamidine hydrochloride, in analogy to the procedures described in examples 101C] to 101F]) to give 2-{4-[4-methoxymethyl-2-(4-trifluoromethyl-phenyl)-pyrimidin-5-ylmethoxy]-2-methyl-phenoxy}-2-methyl-propionic acid ethyl ester, which was subsequently saponified in analogy to the procedure described in example 101B] to yield the title compound as off-white crystalls of mp. 120–121° C.

Sources & evidence

ORD record: ord-48b406bbc071467c9265b5fd39741806
Source dataset: uspto-grants-2006_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07115611B2

Reaction notes

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