N-Hydroxyphthalimide → N-[[5-(benzyloxy)-3,4-dihydro-3-methyl-4-oxo-2-pyrimidinyl]methoxy]phthalimide

HRID 1755870Notes

Reaction equation

N(C(OCC)=O)=NC(OCC)=O.[CH2:13]([O:20][C:21]1[C:22](=[O:30])[N:23]([CH3:29])[C:24]([CH2:27][OH:28])=[N:25][CH:26]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.O[N:32]1[C:36](=[O:37])[C:35]2=[CH:38][CH:39]=[CH:40][CH:41]=[C:34]2[C:33]1=[O:42].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>CC(N(C)C)=O>[CH2:13]([O:20][C:21]1[C:22](=[O:30])[N:23]([CH3:29])[C:24]([CH2:27][O:28][N:32]2[C:33](=[O:42])[C:34]3=[CH:41][CH:40]=[CH:39][CH:38]=[C:35]3[C:36]2=[O:37])=[N:25][CH:26]=1)[C:14]1[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

Conditions

Temperature: 0 °C

Procedure

Diethyl azodicarboxylate (4.8 g) (20 mmol) are added dropwise at 0° C. while stirring to a mixture of 3.69 g (15 mmol) of 5-(benzyloxy)-2-(hydroxymethyl)-3-methyl-4(3H)-pyrimidinone, 3.26 g (20 mmol) of N-hydroxyphthalimide and 5.24 g (20 mmol) of triphenylphosphine in 100 ml of absolute dimethylacetamide. The mixture is stirred at 0° C. for 2 hours and at room temperature for 16 hours. Subsequently, the solvent is removed in a high vacuum at room temperature. The residue is crystallized from ethanol/diethyl ether. After drying in a high vacuum for 18 hours at room temperature there are obtained 5.5 g of N-[[5-(benzyloxy)-3,4-dihydro-3-methyl-4-oxo-2-pyrimidinyl]methoxy]phthalimide as white crystals of m.p. 170° C.

Workup

customSubsequently, the solvent is removed in a high vacuum at room temperature
customThe residue is crystallized from ethanol/diethyl ether
customAfter drying in a high vacuum for 18 hours at room temperature

Sources & evidence

ORD record: ord-0ae1e46b59ac4babae7ffe9eb2b8d8b9
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438052

Reaction notes

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