Ethyl Acetate → HCID 68288489, compound

HRID 1921973Notes

Reaction equation

CN(C)[CH:3]=[CH:4][C:5]([C:7]1[CH:8]=[C:9]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:25])([CH3:24])[CH3:23])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[CH:11]=2)=O.S(O)(O)(=O)=O.[CH3:33][N:34]([CH3:38])[C:35]([NH2:37])=[NH:36].[O-]CC.[Na+].C(OCC)(=O)C>C(O)C>[CH3:33][N:34]([CH3:38])[C:35]1[N:37]=[C:5]([C:7]2[CH:8]=[C:9]([NH:19][C:20](=[O:26])[O:21][C:22]([CH3:24])([CH3:23])[CH3:25])[C:10]3[C:15]([CH:16]=2)=[CH:14][CH:13]=[C:12]([O:17][CH3:18])[CH:11]=3)[CH:4]=[CH:3][N:36]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of tert-butyl (3-(3-(dimethylamino)acryloyl)-7-methoxynaphthalen-1-yl)carbamate (31) (250 mg, 0.67 mmol), and N,N-dimethylguanidine sulfate (220 mg, 0.8 mmol) in ethanol (10 ml) was added 21% wt sodium ethoxide in ethanol (218 μl, 0.67 mmol). The mixture was heated to 80° C. for 24 hours followed by addition of N,N-dimethylguanidine sulfate (110 mg, 0.4 mmol) and 21% wt sodium ethoxide in ethanol (100 μl). After a further 2 days at 80° C. the mixture was poured into ethyl acetate (150 ml) washed with water (100 ml), brine (100 ml) and dried over anhydrous magnesium sulfate. Evaporation to dryness yielded tert-butyl (3-(2-(dimethylamino)pyrimidin-4-yl)-7-methoxynaphthalen-1-yl)carbamate (140) as a pale brown foam (261 mg). 1H NMR (CDCl3) 400 MHz δ 8.41-8.36 (m, 3H), 7.88-7.87 (d, J=8.8 Hz, 1H), 7.52 (m, 2H), 7.19 (dd, J=2.4 and 9.2 Hz 1H), 7.13 (m, 1H), 7.02 (d, J=5.6 Hz, 1H) 6.65 (s, 1H), 3.97 (s, 1H), 3.31 (s, 6H), 1.57 (s, 9H), LCMS m/e 395 (M+H)

Workup

washwashed with water (100 ml), brine (100 ml)
dry with materialdried over anhydrous magnesium sulfate
customEvaporation to dryness

Sources & evidence

ORD record: ord-94b24724406e4fea983e64a8fdcf37b3
Source dataset: uspto-grants-2012_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08173808B2

Reaction notes

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