Methyl acetoacetate → Ethyl 2-(furan-2-yl)-4-(4-fluorophenyl)-6-methyl-1,4-dihyropyrimidin-5-carboxylate

HRID 425252Notes

Reaction equation

Cl.S1C=CC=C1C(N)=N.Cl[C:11]1[CH:18]=[C:17]([F:19])[CH:16]=[CH:15][C:12]=1[CH:13]=O.C(OC)(=O)CC(C)=O.Cl.[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]([NH2:36])=[NH:35].FC1C=CC(C=O)=CC=1.[C:46]([O:52][CH2:53][CH3:54])(=[O:51])[CH2:47][C:48]([CH3:50])=O>>[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]1[NH:36][C:48]([CH3:50])=[C:47]([C:46]([O:52][CH2:53][CH3:54])=[O:51])[CH:13]([C:12]2[CH:15]=[CH:16][C:17]([F:19])=[CH:18][CH:11]=2)[N:35]=1

Participants

Reactant 6

HCID 7757Methyl acetoacetate

HCID 8868Ethyl Acetoacetate

HCID 680234-Fluorobenzaldehyde

HCID 1450242-Chloro-4-fluorobenzaldehyde

HCID 2781759Thiophene-2-carboximidamide Hydrochloride

HCID 12231049Furan-2-carboximidamide hydrochloride

Product 1

HCID 25000908Ethyl 2-(furan-2-yl)-4-(4-fluorophenyl)-6-methyl-1,4-dihyropyrimidin-5-carboxylateYield 29%

Procedure

According to the process of Example 1, except that the 2-thienylformamidine hydrochloride, 2-chloro-4-fluorobenzaldehyde and methyl acetoacetate were replaced by 2-furylformamidine hydrochloride, 4-fluorobenzaldehyde and ethyl acetoacetate, respectively, and 0.21 g of a pale yellow particulates were obtained (yield: 29%); 1H-NMR (400 MHz, CDCl3-d1) δ 7.47-7.46 (d, 1H, J=1.2 Hz, ArH) 7.36-7.32 (t, 2H, J=8.8 Hz, ArH); 7.11 (s, 1H, ArH); 6.98-6.94 (t, 2H, J=8.8 Hz, ArH); 6.52-6.51 (q, 1H, J=1.4 Hz, ArH); 5.69 (s, 1H, CH); 4.12-4.10 (q, 2H, J=7.2 Hz, CH2); 1.21-1.18 (t, 3H, J=7.6 Hz, CH3). MS (EI) 328.1 (M+).

Workup

customrespectively, and 0.21 g of a pale yellow particulates were obtained (yield: 29%)

Sources & evidence

ORD record: ord-5e9c64e1f7c444e099add540ee29b1e3
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106196B2

Reaction notes

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