Phosphate → Di-tert-butyl ((4-(3,4-dichlorophenyl)-2-((2-(1,3-dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)acetyl)imino)thiazol-3(2H)-yl)methyl) phosphate

HRID 338179Notes

Reaction equation

HRID 338179 reaction equation
P([O-])([O-])([O-])=O.[Cl:6][C:7]1[CH:8]=[C:9]([C:14]2[N:15]=[C:16]([NH:19][C:20](=[O:35])[CH2:21][N:22]3[C:30]4[C:29](=[O:31])[N:28]([CH3:32])[C:27](=[O:33])[N:26]([CH3:34])[C:25]=4[N:24]=[CH:23]3)[S:17][CH:18]=2)[CH:10]=[CH:11][C:12]=1[Cl:13].[P:36]([O:48][CH2:49]I)([O:43][C:44]([CH3:47])([CH3:46])[CH3:45])([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])=[O:37].[H-].[Na+]>CN(C=O)C>[P:36]([O:48][CH2:49][N:15]1[C:14]([C:9]2[CH:10]=[CH:11][C:12]([Cl:13])=[C:7]([Cl:6])[CH:8]=2)=[CH:18][S:17][C:16]1=[N:19][C:20](=[O:35])[CH2:21][N:22]1[C:30]2[C:29](=[O:31])[N:28]([CH3:32])[C:27](=[O:33])[N:26]([CH3:34])[C:25]=2[N:24]=[CH:23]1)([O:38][C:39]([CH3:42])([CH3:41])[CH3:40])([O:43][C:44]([CH3:45])([CH3:46])[CH3:47])=[O:37]

Participants

6

Reactant 4

HCID 1061PhosphateHCID 24758Sodium hydrideHCID 5136098N-[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetamideHCID 58196853Di-Tert-Butyl Iodomethyl Phosphate2×

Product 1

HCID 86666698Di-tert-butyl ((4-(3,4-dichlorophenyl)-2-((2-(1,3-dimethyl-2,6-dioxo-2,3-dihydro-1H-purin-7(6H)-yl)acetyl)imino)thiazol-3(2H)-yl)methyl) phosphate

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The title compound was prepared according to the general procedure as described in method A for the preparation of phosphate derivatives by coupling N-[4-(3,4-dichlorophenyl)-1,3-thiazol-2-yl]-2-(1,3-dimethyl-2,6-dioxo-1,2,3,6-tetrahydro-7H-purin-7-yl)acetamide (150 mg, 0.322 mmol) with freshly prepared di-tert-butyl iodomethyl phosphate (Intermediate 2) (395.16 mg, 1.129 mmol) in the presence of sodium hydride (60% dispersion in mineral oil, 20 mg, 0.483 mmol) in dry DMF (2 ml) with to yield 135 mg of pure product as an off-white solid. 1H NMR (300 MHz, CDCl3): δ 1.48 (br s, 18H), 3.35 (s, 3H), 3.47 (s, 2H), 3.62 (s, 3H), 5.71 (s, 2H), 6.36 (br s, 2H), 7.42-7.50 (m, 1H), 7.60-7.72 (m, 1H), 8.02 (s, 1H).

Sources & evidence

ORD record
ord-259b513da4714f20a5c1889670ef8549
Source dataset
uspto-grants-2014_11
Patent number
US08889862B2

Reaction notes

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