Cyclopropanecarboxamide → 4-Chloro-2-cyclopropyl-5-(2-methoxyphenyl)thieno[2,3-d]pyrimidine

HRID 928591Notes

Reaction equation

[NH2:1][C:2]1[S:3][CH:4]=[C:5]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=2[O:18][CH3:19])[C:6]=1[C:7](OCC)=O.[CH:20]1([C:23]([NH2:25])=O)[CH2:22][CH2:21]1.[P+2](Cl)(Cl)[Cl:27]>C(Cl)Cl>[Cl:27][C:7]1[C:6]2[C:5]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][CH3:19])=[CH:4][S:3][C:2]=2[N:1]=[C:23]([CH:20]2[CH2:22][CH2:21]2)[N:25]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Ethyl 2-amino-4-(2-methoxyphenyl)thiophene-3-carboxylate (1 g, 3.606 mmol), cyclopropanecarboxamide (0.3069 g, 3.606 mmol) and phosphorous (V) trichloride (0.6723 mL, 7.212 mmol) were combined and heated to 100° C. over the weekend in a Reactivial. The reaction mixture was diluted with DCM (25 mL), washed with water (2×25 mL), dried over Na2SO4 and concentrated at reduced pressure. The resulting residue was purified by flash chromatography, eluting with a gradient of petroleum ether to 50/50 petroleum ether/ethyl acetate to afford 4-chloro-2-cyclopropyl-5-(2-methoxyphenyl)thieno[2,3-d]pyrimidine (0.51 g). LCMS: purity 100%, RT=4.63 min, M+1=317.0

Workup

washwashed with water (2×25 mL)
dry with materialdried over Na2SO4
concentrationconcentrated at reduced pressure
customThe resulting residue was purified by flash chromatography
washeluting with a gradient of petroleum ether to 50/50 petroleum ether/ethyl acetate

Sources & evidence

ORD record: ord-3bdd8f3589f940da98fcb4afe45af1b0
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09290511B2

Reaction notes

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