Sodium hydride → HCID 21934627, compound

HRID 1241388Notes

Reaction equation

HRID 1241388 reaction equation
[O:1]=[C:2]([N:17]1[CH2:21][CH2:20][CH2:19][CH2:18]1)[CH2:3][N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH2:16])[CH:11]=2)[CH2:6][CH2:5]1.[H-].[Na+].Cl[C:25]1[S:26][C:27]([C:30]#[N:31])=[CH:28][N:29]=1>>[O:1]=[C:2]([N:17]1[CH2:18][CH2:19][CH2:20][CH2:21]1)[CH2:3][N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:15]=[CH:14][N:13]=[C:12]([NH:16][C:25]3[S:26][C:27]([C:30]#[N:31])=[CH:28][N:29]=3)[CH:11]=2)[CH2:8][CH2:9]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21934631HCID 21934631, compound

Product 1

HCID 21934627HCID 21934627, compound

Procedure

6-[4-(2-Oxo-2-pyrrolidin-1-ylethyl)piperazin-1-yl]pyrimidin-4-amine 17-2 (0.60 g, 2.07 mmol) and sodium hydride (0.165 g, 4.13 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.299 g, 2.07 mmol) were treated as in Scheme 4 above. The product was purified on a silica column. Hi-Res MS: calc: 399.1710 found: 399.1706. 1NMR (CDCl3): 9.40 ppm (s, 1H); 8.45 ppm (s, 1H); 7.88 ppm (s, 1H); 5.98 ppm (s, 1H); 3.68 ppm (s, 4H); 3.50 ppm (m, 4H); 3.21 ppm (s, 2H); 2.68 ppm (t, 4H); 1.98 ppm (m, 2H); 1.87 ppm (m, 2H).

Workup

  1. customThe product was purified on a silica column

Sources & evidence

ORD record
ord-198901bd3c0941adaec14e164b791c14
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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