Boron tribromide → HCID 19918009, compound

HRID 1755871Notes

Reaction equation

C([O:8][C:9]1[C:10](=[O:29])[N:11]([CH3:28])[C:12]([CH2:15][O:16][N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])=[N:13][CH:14]=1)C1C=CC=CC=1.B(Br)(Br)Br>ClCCl>[OH:8][C:9]1[C:10](=[O:29])[N:11]([CH3:28])[C:12]([CH2:15][O:16][N:17]2[C:21](=[O:22])[C:20]3=[CH:23][CH:24]=[CH:25][CH:26]=[C:19]3[C:18]2=[O:27])=[N:13][CH:14]=1

Participants

Conditions

Temperature: -70 °C

Procedure

N-[[5-(Benzyloxy)-3,4-dihydro-3-methyl-4-oxo-2-pyrimidinyl]methoxy]phthalimide (1.56 g) (4 mmol) are dissolved in 110 ml of dichloromethane and treated dropwise at about -70° C. while stirring with 0.42 ml (4.4 mmol) of boron tribromide. After stirring at about -70° C. for 4 hours and at room temperature for 16 hours the solvent is removed in a water-jet vacuum at room temperature. The residue is treated with about 30 ml of water, the insoluble product is filtered off and washed firstly with water and subsequently with diethyl ether. After drying in a high vacuum at room temperature for 18 hours there are obtained 1.1 g of N-[(3,4-dihydro-5-hydroxy-3-methyl-4-oxo-2-pyrimidinyl)methoxy]phthalimide as a white powder, m.p. 172° C. (dec.).

Workup

additiontreated dropwise at about -70° C.
customis removed in a water-jet vacuum at room temperature
additionThe residue is treated with about 30 ml of water
filtrationthe insoluble product is filtered off
washwashed firstly with water and subsequently with diethyl ether
customAfter drying in a high vacuum at room temperature for 18 hours there

Sources & evidence

ORD record: ord-2ecbe721c55b497ba8e6792ce42527bb
Source dataset: uspto-grants-1995_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05438052

Reaction notes

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