Sodium hydride → HCID 21934688, compound

HRID 1241363Notes

Reaction equation

HRID 1241363 reaction equation
[C:1]([N:4]1[CH2:9][CH2:8][N:7]([C:10]2[N:15]=[C:14]([NH2:16])[CH:13]=[CH:12][N:11]=2)[CH2:6][CH2:5]1)(=[O:3])[CH3:2].[H-].[Na+].Cl[C:20]1[S:21][C:22]([C:25]#[N:26])=[CH:23][N:24]=1>CO>[C:1]([N:4]1[CH2:5][CH2:6][N:7]([C:10]2[N:15]=[C:14]([NH:16][C:20]3[S:21][C:22]([C:25]#[N:26])=[CH:23][N:24]=3)[CH:13]=[CH:12][N:11]=2)[CH2:8][CH2:9]1)(=[O:3])[CH3:2]

Participants

5

Reactant 3

HCID 24758Sodium hydride2×HCID 14852222-Chlorothiazole-5-carbonitrileHCID 130944181-[4-(4-Aminopyrimidin-2-yl)piperazin-1-yl]ethan-1-one

Product 1

HCID 21934688HCID 21934688, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
25 °C

Procedure

2-(4-acetylpiperazin-1-yl)pyrimidin-4-amine 4-4 (0.1 g, 0.45 mmol) was dissolved in dry TBF and then 1 equivalent of sodium hydride (0.036 g, 0.45 mmol) was added and this was stirred for 20 minutes at 25° C. then 2-chloro-1,3-thiazole-5-carbonitrile 2-2 (0.065 g, 0.45 mmol) was added followed immediately by 1 more equivalent of sodium hydride. The reaction was then stirred at 100° C. for 3 hours. The reaction was cooled to 25° C. and methanol was added. This solution was loaded directly onto a silica column and eluted with DCM:MeOH:NH4OH (95:5:0.5). Fractions were combined and evaporated to yield the product, 4-5. Hi-Res MS: calc: 330.1132 found: 330.1137. 1H-NMR (DMSO): 8.33 ppm (s, 1H); 8.19 ppm (d, 1H); 6.34 ppm (d, 1H); 3.88 ppm (m, 2H); 3.80 ppm (m, 2H); 3.57 ppm (m, 4H); 2.07 ppm (s, 3H).

Workup

  1. stirringThe reaction was then stirred at 100° C. for 3 hours
  2. temperatureThe reaction was cooled to 25° C.
  3. washeluted with DCM:MeOH:NH4OH (95:5:0.5)
  4. customevaporated
  5. customto yield the product, 4-5

Sources & evidence

ORD record
ord-ad482be79f8842d8865c5d3f2d1210d0
Source dataset
uspto-grants-2006_10
Patent number
US07115597B2

Reaction notes

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