Benzaldehyde → Ethyl 2-(2-furanyl)-6-methyl-4-phenyl-1,4-dihydropyrimidine-5-carboxylate

HRID 425253Notes

Reaction equation

Cl.S1C=CC=C1C(N)=N.Cl[C:11]1[CH:18]=[C:17](F)[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].C(=O)C1C=CC=CC=1.[C:45]([O:51][CH2:52][CH3:53])(=[O:50])[CH2:46][C:47]([CH3:49])=O>>[O:29]1[CH:33]=[CH:32][CH:31]=[C:30]1[C:34]1[NH:36][C:47]([CH3:49])=[C:46]([C:45]([O:51][CH2:52][CH3:53])=[O:50])[CH:13]([C:12]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:11]=2)[N:35]=1

Participants

Reactant 6

HCID 240Benzaldehyde

HCID 7757Methyl acetoacetate

HCID 8868Ethyl Acetoacetate

HCID 1450242-Chloro-4-fluorobenzaldehyde

HCID 2781759Thiophene-2-carboximidamide Hydrochloride

HCID 12231049Furan-2-carboximidamide hydrochloride

Product 1

HCID 25000558Ethyl 2-(2-furanyl)-6-methyl-4-phenyl-1,4-dihydropyrimidine-5-carboxylateYield 32%

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, benzaldehyde and ethyl acetoacetate, respectively, and 0.21 g of a pale yellow particulates were obtained (yield: 32%); 1H-NMR (400 MHz, CDCl3-d1) δ 7.45 (s, 1H, ArH); 7.39-7.37 (d, 2H, J=7.2 Hz, ArH); 7.30-7.21 (m, 3H, J=7.2 Hz, ArH); 7.09 (s, 1H, ArH); 6.50 (m, 1H, ArH), 5.71 (s, 1H, CH); 4.12-4.09 (q, 2H, J=7.2 Hz, CH2); 2.45 (s, 3H, CH3): 1.21-1.17 (t, 3H, J=7.2 Hz, CH3). MS (EI) 310.2 (M+).

Workup

customrespectively, and 0.21 g of a pale yellow particulates were obtained (yield: 32%)

Sources & evidence

ORD record: ord-72222aaec69a43b79604855e115eb6f2
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106196B2

Reaction notes

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