Ethanolamine → 8-(Aminomethyl)-10-(5-chlorofuran-2-yl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-7,8-dihydro-1H-pyrimido[4',5':3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione

HRID 624582Notes

Reaction equation

C(CN)O.[Cl:5][C:6]1[O:10][C:9]([CH:11]2[C:16]3=[C:17]4[N:29]([CH3:30])[C:28](=[O:31])[N:27]([CH3:32])[C:26](=[O:33])[C:18]4=[C:19]([C:20]4[S:21][CH:22]=[C:23]([CH3:25])[N:24]=4)[N:15]3[CH2:14][CH:13]([CH2:34][N:35]3C(=O)C4C(=CC=CC=4)C3=O)[O:12]2)=[CH:8][CH:7]=1>C1(C)C=CC=CC=1.O>[NH2:35][CH2:34][CH:13]1[O:12][CH:11]([C:9]2[O:10][C:6]([Cl:5])=[CH:7][CH:8]=2)[C:16]2=[C:17]3[N:29]([CH3:30])[C:28](=[O:31])[N:27]([CH3:32])[C:26](=[O:33])[C:18]3=[C:19]([C:20]3[S:21][CH:22]=[C:23]([CH3:25])[N:24]=3)[N:15]2[CH2:14]1

Participants

Conditions

Temperature: 70 °C

Procedure

Ethanolamine (108 μl, 1.790 mmol) was added to a solution of 10-(5-chlorofuran-2-yl)-8-((1,3-dioxoisoindolin-2-yl)methyl)-1,3-dimethyl-5-(4-methylthiazol-2-yl)-7,8-dihydro-1H-pyrimido[4′,5′:3,4]pyrrolo[2,1-c][1,4]oxazine-2,4(3H,10H)-dione (106 mg, 0.179 mmol) in toluene (3087 μl). The mixture was stirred at 70° C. for 6.5 hours then at room temperature for 16 hours. The mixture was diluted with water (50 ml) and extracted with ethyl acetate (50 ml). The organic phase was washed with 1M NaOH(aq) (20 ml) passed through a hydrophobic frit and evaporated under vacuum to afford the title compound as a mixture of diastereomers.

Workup

waitat room temperature for 16 hours
extractionextracted with ethyl acetate (50 ml)
washThe organic phase was washed with 1M NaOH(aq) (20 ml)
customevaporated under vacuum

Sources & evidence

ORD record: ord-5d957e5998ac47c98b7b67313a1bf873
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09303035B2

Reaction notes

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