Formamidine acetate → tert-Butyl 4-oxo-3,5,6,8-tetrahydropyrido[4',3':4,5]thieno[2,3-d]pyrimidine-7(4H)-carboxylate

HRID 1887408Notes

Reaction equation

C([O:3][C:4]([C:6]1[C:14]2[CH2:13][CH2:12][N:11]([C:15]([O:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[O:16])[CH2:10][C:9]=2[S:8][C:7]=1[NH2:22])=O)C.C(O)(=O)C.[CH:27](N)=[NH:28]>CN(C=O)C>[C:18]([O:17][C:15]([N:11]1[CH2:10][C:9]2[S:8][C:7]3[N:22]=[CH:27][NH:28][C:4](=[O:3])[C:6]=3[C:14]=2[CH2:13][CH2:12]1)=[O:16])([CH3:21])([CH3:20])[CH3:19]

Participants

Conditions

Temperature: 100 °C

Procedure

To a 2-Amino-4,7-dihydro-5H-thieno[2,3-c]pyridine-3,6-dicarboxylic acid 6-tert-butyl ester 3-ethyl ester (5.0 g, 15 mmol) in DMF (50 mL) solution was added formamidine acetate (2.39 g, 23 mmol, 1.5 equiv). The mixture was heated at 100° C. in an oil bath for overnight. The reaction mixture was cooled to rt and then concentrated in vacuo. Ethyl acetate (50 mL) was added to the reaction solid mixture and stirred at rt for 2 h. The mixture was then filtered, rinsed with ethyl acetate (25 mL). The solid was placed in a vacuum oven and dried for overnight to yield a white solid (4.17 g, 90.6%). 1H NMR (CD3OD-d4) δ 8.05 (s, 1H), 4.57 (s, 2H), 3.61 (t, 2H), 2.92 (t, 2H), 1.42 (s, 9H); LCMS RT=2.78 min, [M+H]+=308.0.

Workup

temperatureThe reaction mixture was cooled to rt
concentrationconcentrated in vacuo
additionEthyl acetate (50 mL) was added to the reaction solid mixture
filtrationThe mixture was then filtered
washrinsed with ethyl acetate (25 mL)
customdried for overnight

Sources & evidence

ORD record: ord-a6ed71b8c39d4507afd81b1573f84dd6
Source dataset: uspto-grants-2013_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08501755B2

Reaction notes

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