Boron tribromide → 2-Anilino-4-hydroxymethyl-6-cyclopropylpyrimidine

HRID 358801Notes

Reaction equation

[NH:1]([C:8]1[N:13]=[C:12]([CH2:14][O:15]C)[CH:11]=[C:10]([CH:17]2[CH2:19][CH2:18]2)[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1C=CC(NC(N)=N)=CC=1.C1(C(=O)CC(=O)COC)CC1.B(Br)(Br)Br>ClCCl>[NH:1]([C:8]1[N:13]=[C:12]([CH2:14][OH:15])[CH:11]=[C:10]([CH:17]2[CH2:18][CH2:19]2)[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -68 °C

Procedure

5.9 g (23 mmol) of 2-anilino-4-methoxymethyl-6-cyclopropylpyrimidine, prepared from phenylguanidine and 1-cyclopropyl-4-methoxy-1,3-butanedione, are dissolved in 200 ml of dichloromethane and the solution is cooled to -68° C. 6.8 g (27 mmol) of boron tribromide are slowly added dropwise to the salmon-coloured solution within a period of half an hour, with vigorous stirring, and the cooling bath is then removed and stirring is continued for a further 2 hours at room temperature. After the addition of 150 g of ice-water, the precipitated crude product is filtered off and recrystallised from methanol using active carbon. The light-yellow crystals melt at 124°-126° C. Yield: 4.7 g (19.5 mmol; 84.7% of the theoretical yield).

Workup

customthe cooling bath is then removed
additionAfter the addition of 150 g of ice-water
customthe precipitated crude product
filtrationis filtered off
customrecrystallised from methanol using active carbon
custommelt at 124°-126° C
custom84.7% of the theoretical yield)

Sources & evidence

ORD record: ord-009af4769cd641a2989585029c679fdd
Source dataset: uspto-grants-1991_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04997941

Reaction notes

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