4-Toluenesulfonyl chloride → HCID 22001642, compound

HRID 324983Notes

Reaction equation

[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[NH:11][C:10]([CH3:15])=[N:9][C:8]=2[N:7]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4].[C:21]1([CH3:31])[CH:26]=[CH:25][C:24]([S:27](Cl)(=[O:29])=[O:28])=[CH:23][CH:22]=1.[K+].[Br-]>>[CH2:1]([N:5]1[C:13](=[O:14])[C:12]2[N:11]([S:27]([C:24]3[CH:25]=[CH:26][C:21]([CH3:31])=[CH:22][CH:23]=3)(=[O:29])=[O:28])[C:10]([CH3:15])=[N:9][C:8]=2[N:7]([CH2:16][CH2:17][CH2:18][CH3:19])[C:6]1=[O:20])[CH2:2][CH2:3][CH3:4]

Participants

Reactant 3

HCID 73974-Toluenesulfonyl chloride

HCID 253877Potassium Bromide

HCID 22001644HCID 22001644, compound

Product 1

HCID 22001642HCID 22001642, compoundYield 75%

Procedure

The title compound was prepared according to the procedure of example 3 except that 1,3-dibutyl-8-methyl-3,7-dihydro-purine-2,6-dione was used in place of 1,3-dibutyl-3,7-dihydro-purine-2,6-dione and p-toluenesulfonyl chloride was used in place of methanesulfonyl chloride. Yield: 75%; mp: 111-113° C.; 1H NMR (300 MHz, CDCl3): δ 0.89-0.96 (m, 6H), 1.29-1.37 (m, 4H), 1.58-1.65 (m, 2H), 1.67-1.72 (m, 2H), 2.48 (s, 3H), 2.86 (s, 3H), 3.93 (t, J=7.6 Hz, 2H), 4.11 (t, J=7.1 Hz, 2H), 7.36 (d, J=8.1 Hz, 2H), 8.13 (d, J=8.5 Hz, 2H); IR (KBr, cm−1): 2960m, 2865m, 1709s, 1674s, 1593m, 1528s, 1479m, 1181m, 1121s, 938m, 760m, 595m; MS (ES) m/z (relative intensity): 433 (M++H, 100).

Sources & evidence

ORD record: ord-7305cd7cee5e4d24a90328bb73d9d181
Source dataset: uspto-grants-2001_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06221874B1

Reaction notes

Loading…