Water → HCID 178478412, compound

HRID 1742770Notes

Reaction equation

[Cl:1][C:2]1[N:7]=[C:6]([O:8][CH:9]2[CH2:14][CH2:13][CH2:12][CH2:11][CH2:10]2)[N:5]=[C:4]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)[CH:3]=1.C([Li])CCC.[Cl-:27].[Cl-].[CH:29]1([Ti+2:34][CH:35]2[CH:39]=[CH:38][CH:37]=[CH:36]2)[CH:33]=[CH:32][CH:31]=[CH:30]1.O>C1COCC1>[Cl:27][Ti:34]([CH:29]1[CH:30]=[CH:31][CH:32]=[CH:33]1)([CH:35]1[CH:39]=[CH:38][CH:37]=[CH:36]1)[C:3]1[C:4]([O:15][CH:16]2[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]2)=[N:5][C:6]([O:8][CH:9]2[CH2:10][CH2:11][CH2:12][CH2:13][CH2:14]2)=[N:7][C:2]=1[Cl:1]

Participants

Conditions

Temperature: -40 °C

Procedure

6.15 g (19.8 mmol) of 6-chloro-2,4-bis(cyclohexyloxy)pyrimidine are dissolved in 40 ml of THF under argon as protective gas, the solution is cooled to -40° C., and 12.4 ml of n-butyllithium (1.6M/hexane) are added dropwise. 2.25 g (9 mmol) of solid biscyclopentadienyltitanium dichloride are added to the resultant solution at -40° C. The reaction mixture is allowed to warm slowly from -40° C. to 25° C., is then poured into 40 ml of water and is filtered through ®Hyflo. The aqueous phase is separated off, and the organic phase is dried using magnesium sulfate, filtered and evaporated on a rotary evaporator. The residue is separated by flash chromatography (SiO2), giving 1.0 g of the compound from Example 63 and 0.9 g of the title compound, having a melting range of 145°-155 ° C.

Workup

temperatureto warm slowly from -40° C. to 25° C.
filtrationis filtered through ®Hyflo
customThe aqueous phase is separated off
customthe organic phase is dried
filtrationfiltered
customevaporated on a rotary evaporator
customThe residue is separated by flash chromatography (SiO2)

Sources & evidence

ORD record: ord-e80d54d08a1b4776aa1dd49e6e737ba5
Source dataset: uspto-grants-1994_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05340701

Reaction notes

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