Carbon Tetrachloride → HCID 18446624, compound

HRID 1269058Notes

Reaction equation

HRID 1269058 reaction equation
[CH:1]1([NH:6][C:7]2[N:12]=[C:11]([C:13]3[C:14]([C:22]4[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH:29]([CH3:31])[CH3:30])[CH:23]=4)=[N:15][N:16]4[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=34)[CH:10]=[CH:9][N:8]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.C([Li])CCC.C(Cl)(Cl)(Cl)[Cl:38]>>[Cl:38][C:21]1[N:16]2[N:15]=[C:14]([C:22]3[CH:27]=[CH:26][N:25]=[C:24]([NH:28][CH:29]([CH3:31])[CH3:30])[CH:23]=3)[C:13]([C:11]3[CH:10]=[CH:9][N:8]=[C:7]([NH:6][CH:1]4[CH2:2][CH2:3][CH2:4][CH2:5]4)[N:12]=3)=[C:17]2[CH:18]=[CH:19][CH:20]=1

Participants

4

Reactant 3

HCID 5943Carbon TetrachlorideHCID 18446640HCID 18446640, compoundHCID 178418339Butyllithium

Product 1

HCID 18446624HCID 18446624, compoundYield 78%

Procedure

In a similar manner as described in Example 17 from N-cyclopentyl-4-{2-[2-(isopropylamino)-4-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl}-2-pyrimidinamine (166 mg, 0.401 mmol), n-butyllithium (753 μL, 1.6 M in hexanes, 1.20 mmol) and carbon tetrachloride (155 μL, 1.60 mmol) was formed 4-{7-chloro-2-[2-(isopropylamino)-4-pyridinyl]pyrazolo[1,5-a]pyridin-3-yl}-N-cyclopentyl-2-pyrimidinamine (140 mg, 78%). Rf 0.21 (1:1 hexanes:ethyl acetate); 1H NMR (CDCl3) δ 8.36 (d, 1H), 8.19 (d, 1H), 8.07 (d, 1H), 7.36 (m, 1H), 7.13 (d, 1H), 6.90 (d, 1H), 6.81 (s, 1H), 6.52 (d, 1H), 5.25–5.21 (br, 2H), 4.35 (m, 1H), 3.89 (m, 1H), 2.18–2.04 (m, 2H), 1.80–1.50 (m, 6H), 1.22 (d, 6H).

Sources & evidence

ORD record
ord-9f209e36259d425f8d1f75eafc18eb96
Source dataset
uspto-grants-2007_04
Patent number
US07199120B2

Reaction notes

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