Sodium hydride → HCID 58739083, compound

HRID 720283Notes

Reaction equation

HRID 720283 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8](S(C)(=O)=O)[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[O:5])[CH3:2].[S:26]1(=[O:33])(=[O:32])[CH2:31][CH2:30][CH2:29][CH2:28][NH:27]1.[H-].[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([N:27]2[CH2:28][CH2:29][CH2:30][CH2:31][S:26]2(=[O:33])=[O:32])[N:9]([CH3:21])[C:10](=[O:20])[C:11]=1[O:12][CH2:13][C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 3035081,4-ButanesultamHCID 21060065HCID 21060065, compound

Product 1

HCID 58739083HCID 58739083, compoundYield 92.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Reaction of 2-methanesulfonyl-5-benzyloxy-1-methyl-6-oxo-1,6-dihydro-pyrimidine-4-carboxylic acid ethyl ester (2.21 g, 6.03 mmol) and [1,2]thiazinane 1,1-dioxide (0.97 g, 7.2 mmol) in dry N,N-dimethylformamide (30 ml) with sodium hydride (0.35 g of a 60% dispersion in mineral oil, 8.8 mmol) gave 2.35 g (92% yield) of the title ester as white needles; mp 109–110° C. 1HNMR 400 MHz (CDCl3) δ (ppm): 1.29 (3H, t, J=7.1 Hz, CH3), 1.62 (1H, m, CH), 2.3–2.6 (3H, m, CH2 and CH), 3.15–3.21 (1H, m, CH), 3.5–3.6 (1H, m, CH), 3.64 (3H, s, NCH3), 3.64 (1H, m overlapping with NCH3, CH), 3.97–4.05 (1H, m, CH), 4.32 (2H, q, J=7.1 Hz, OCH2), 5.29 (2H, AB system, JAB=10.6 Hz, Δν=62.5 Hz, OCH2), 7.3–7.5 (5H, m, aromatics). Anal. Calcd for C19H23N3O6S: C 54.15, H 5.50, N 9.97. Found: C 53.88, H 5.40, N 9.91.

Sources & evidence

ORD record
ord-52e8d9cd4de44802b7e72eaeab1728e3
Source dataset
uspto-grants-2006_11
Patent number
US07135467B2

Reaction notes

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