Cyclopropanemethanol → HCID 10254335, compound

HRID 750813Notes

Reaction equation

HRID 750813 reaction equation
CS([C:5]1[N:10]=[C:9]([N:11]2[CH2:15][CH2:14][CH2:13][CH2:12]2)[C:8]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=2)=[C:7]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=2[Cl:30])[N:6]=1)(=O)=O.[CH:31]1([CH2:34][OH:35])[CH2:33][CH2:32]1>>[CH:31]1([CH2:34][O:35][C:5]2[N:10]=[C:9]([N:11]3[CH2:15][CH2:14][CH2:13][CH2:12]3)[C:8]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=3)=[C:7]([C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][C:24]=3[Cl:30])[N:6]=2)[CH2:33][CH2:32]1

Participants

3

Reactant 2

HCID 75644CyclopropanemethanolHCID 69197659HCID 69197659, compound

Product 1

HCID 10254335HCID 10254335, compound

Procedure

2-(Methylsulfonyl)-4-(N-pyrrolidinyl)-5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)pyrimidine (Example 36, Step A, 48 mg, 0.1 mmol) was treated with cyclopropyl methanol by the same general procedure described in Reference Examples 6 and 7. Workup and flash column chromatography on silica gel (eluted with 70/30 hexanes/ethyl acetate) afforded the title compound. HPLC: Rt=3.46 min. 1H-NMR 500 MHz (CDCl3): δ 0.37 (d, J=4 Hz, 2H), 0.61 (dd, J=8 Hz, J=1 Hz, 2H), 1.38 (m, 1H), 1.80 (bs, 4H), 3.2 (bs, 4H), 4.17 (m, 1H), 4.25 (m, 1H), 6.85 (d, J=8 Hz, 1H), 7.08 (d over bs, J=8 Hz, 3H), 7.12 (d, J=8 Hz, 2H) 7.24 (d, J=2 Hz, 1H).

Sources & evidence

ORD record
ord-41c19e0016654ba8affeb7622ff88a2f
Source dataset
uspto-grants-2008_07
Patent number
US07405221B2

Reaction notes

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