2-Chlorobenzaldehyde → Ethyl 2-(furan-2-yl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyrimidin-5-carboxylate

HRID 425251Notes

Reaction equation

Cl.S1C=CC=C1C(N)=N.[Cl:10][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].ClC1C=CC=CC=1C=O.[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][CH:17]=[CH:18][C:11]=2[Cl:10])[N:35]=1

Participants

Reactant 6

HCID 69962-Chlorobenzaldehyde

HCID 7757Methyl acetoacetate

HCID 8868Ethyl Acetoacetate

HCID 1450242-Chloro-4-fluorobenzaldehyde

HCID 2781759Thiophene-2-carboximidamide Hydrochloride

HCID 12231049Furan-2-carboximidamide hydrochloride

Product 1

HCID 25000909Ethyl 2-(furan-2-yl)-4-(2-chlorophenyl)-6-methyl-1,4-dihydropyrimidin-5-carboxylateYield 28%

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, 2-chlorobenzaldehyde and ethyl acetoacetate, respectively, and 0.20 g of a pale yellow particulates were obtained (yield: 28%); 1H-NMR (400 MHz, CDCl3-d1) δ 7.45 (s, 1H, ArH); 7.37-7.34 (m, 2H, ArH); 7.20-7.10 (m, 2H, ArH); 6.48 (m, 1H, ArH); 6.09 (s, 1H, CH); 4.07-4.03 (q, 2H, J=7.2 Hz, CH2); 2.55 (s, 3H, CH3); 1.13-1.09 (t, 3H, J=7.2 Hz, CH3). MS (EI) 344.0 (M+).

Workup

customrespectively, and 0.20 g of a pale yellow particulates were obtained (yield: 28%)

Sources & evidence

ORD record: ord-3c78d7f43ac44d77a8abfde45c202244
Source dataset: uspto-grants-2012_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08106196B2

Reaction notes

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