N,N,N',N'-Tetramethylmethanediamine → HCID 19042922, compound

HRID 1683296Notes

Reaction equation

HRID 1683296 reaction equation
CN(CN(C)C)C.C(Cl)(=O)C.[CH3:12][O:13][C:14]1[CH:19]=[CH:18][N:17]=[C:16]([O:20][C:21]2[CH:22]=[C:23]3[C:27](=[CH:28][CH:29]=2)[NH:26][CH:25]=[CH:24]3)[N:15]=1.C[N:31]([CH2:33][C:34]1C2C(=CC=C(OC3N=C(OC)C=CN=3)C=2)NC=1)C.[C-]#N.[K+].CI>C(Cl)Cl.CN(C=O)C>[C:33]([CH2:34][C:24]1[C:23]2[C:27](=[CH:28][CH:29]=[C:21]([O:20][C:16]3[N:15]=[C:14]([O:13][CH3:12])[CH:19]=[CH:18][N:17]=3)[CH:22]=2)[NH:26][CH:25]=1)#[N:31]

Participants

9

Reactant 6

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6328Methyl iodideHCID 6367Acetyl chlorideHCID 9032Potassium CyanideHCID 19042885HCID 19042885, compoundHCID 19042903HCID 19042903, compound

Product 1

HCID 19042922HCID 19042922, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (1.18 g, 1.58 mL, 11.5 mmol) in CH2Cl2 (10 mL) with acetyl chloride (0.90 g, 0.81 mL, 11.5 mmol) followed by a solution of 5-(4-methoxypyrimidin-2-yloxy)indole (2.0 g, 8.2 mmol) in CH2Cl2 (100 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)-5-(4-methoxypyrimidin-2-yloxy)indole as a white solid. This was treated with finely ground potassium cyanide (1.75 g, 26.8 mmol) and methyl iodide (3.80 g, 1.65 mL, 26.8 mmol) in DMF (130 mL) for 16 hr, and after appropriate work-up, 3-cyanomethyl-5-(4-methoxypyrimidin-2-yloxy)indole was obtained as a white solid, 2.20 g (96%).

Workup

  1. customgave after work-up

Sources & evidence

ORD record
ord-34bed4b39d814298a815148be9a17529
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

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