Potassium thiocyanate → HCID 178504223, compound

HRID 1524752Notes

Reaction equation

CS(O[CH2:6][C@H:7]1[CH2:12][CH2:11][C@@H:10]([N:13]2[CH:17]=[C:16]([C:18]3[C:19]4[CH:26]=[CH:25][N:24]([CH2:27][O:28][CH2:29][CH2:30][Si:31]([CH3:34])([CH3:33])[CH3:32])[C:20]=4[N:21]=[CH:22][N:23]=3)[CH:15]=[N:14]2)[CH2:9][CH2:8]1)(=O)=O.[S-:35][C:36]#[N:37].[K+]>CS(C)=O>[CH3:32][Si:31]([CH3:33])([CH3:34])[CH2:30][CH2:29][O:28][CH2:27][N:24]1[C:20]2[N:21]=[CH:22][N:23]=[C:18]([C:16]3[CH:15]=[N:14][N:13]([C@@H:10]4[CH2:9][CH2:8][C@H:7]([CH2:6][S:35][C:36]#[N:37])[CH2:12][CH2:11]4)[CH:17]=3)[C:19]=2[CH:26]=[CH:25]1

Participants

Conditions

Temperature: 68 °C

Procedure

cis-4-[4-(7-[2-(Trimethylsilyl)ethoxy]methyl-7H-pyrrolo[2,3-d]pyrimidin-4-yl)-1H-pyrazol-1-yl]cyclohexylmethyl methanesulfonate (0.10 g, 0.00020 mol) was dissolved in DMSO (1.00 mL) with potassium thiocyanate (0.082 g, 0.00084 mol). The reaction was heated at 68° C. for 4 days at which time LCMS analysis showed ˜4:1 product/starting material ratio. The reaction was extracted with ethyl acetate and the organic extracts were washed with water, saturated NaCl, dried (MgSO4) and concentrated in vacuo. The concentrate was chromatographed on silica gel using 1:1 EtOAc/hexanes to give the product. LC/MS (M+H)+: 469, 1H NMR (CDCl3): δ 8.89 (s, 1H), 8.36 (s, 1H), 8.31 (s, 1H), 7.45 (d, 1H), 6.87 (d, 1H), 5.73 (S, 2H), 4.45 (m, 1H), 3.60 (m, 2H), 3.05 (m, 2H), 2.37 (m, 2H), 2.10 (m, 4H), 1.70-1.93 (m, 3H), 0.98 (m, 2H), 0.00 (s, 9H).

Workup

extractionThe reaction was extracted with ethyl acetate
washthe organic extracts were washed with water, saturated NaCl
dry with materialdried (MgSO4)
concentrationconcentrated in vacuo
customThe concentrate was chromatographed on silica gel using 1:1 EtOAc/hexanes
customto give the product

Sources & evidence

ORD record: ord-ce75e85dbd8e4daa88d13b2ca8096f34
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09079912B2

Reaction notes

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