Sodium hydride → HCID 9909240, compound

HRID 1241407Notes

Reaction equation

HRID 1241407 reaction equation
[O:1]=[S:2]1(=[O:20])[CH2:6][CH2:5][CH:4]([N:7]2[CH2:12][CH2:11][N:10]([C:13]3[N:18]=[CH:17][N:16]=[C:15]([NH2:19])[CH:14]=3)[CH2:9][CH2:8]2)[CH2:3]1.[H-].[Na+].Cl[C:24]1[S:25][C:26]([C:29]#[N:30])=[CH:27][N:28]=1>>[O:20]=[S:2]1(=[O:1])[CH2:6][CH2:5][CH:4]([N:7]2[CH2:8][CH2:9][N:10]([C:13]3[N:18]=[CH:17][N:16]=[C:15]([NH:19][C:24]4[S:25][C:26]([C:29]#[N:30])=[CH:27][N:28]=4)[CH:14]=3)[CH2:11][CH2:12]2)[CH2:3]1

Participants

4

Reactant 3

HCID 24758Sodium hydrideHCID 14852222-Chlorothiazole-5-carbonitrileHCID 21059981HCID 21059981, compound

Product 1

HCID 9909240HCID 9909240, compound

Procedure

6-[4-(1,1-Dioxidotetrahydrothien-3-yl)piperazin-1-yl]pyrimidin-4-amine 39-2 (0.30 g, 1.01 mmol), sodium hydride (0.081 g, 2.02 mmol) and 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.14 g, 1.01 mmol) were treated as in Scheme 4 above. The product was purified on a C18 column. Hi-Res MS: calc: 406.1114 found: 406.1105. 1H-NMR: 8.46(s, 1H); 8.01(s, 1H); 6.24(s, 1H); 3.86(br s, 6H); 3.59(m, 1H); 3.39(m, 1H); 3.27(m, 1H); 3.17(complex, 4H); 2.70(m, 1H); 2.29(m, 1H).

Workup

  1. customThe product was purified on a C18 column

Sources & evidence

ORD record
ord-4b6a72f0eb094066bd521b91d459fb83
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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