N,N,N',N'-Tetramethylmethanediamine → HCID 19042906, compound

HRID 1683293Notes

Reaction equation

HRID 1683293 reaction equation
CN(CN(C)C)C.C(Cl)(=O)C.[N:12]1[CH:17]=[CH:16][CH:15]=[N:14][C:13]=1[O:18][C:19]1[CH:20]=[C:21]2[C:25](=[CH:26][CH:27]=1)[NH:24][CH:23]=[CH:22]2.C[N:29]([CH2:31][C:32]1C2C(=CC=C(OC3N=CC=CN=3)C=2)NC=1)C.[C-]#N.[K+].CI>C(Cl)Cl.CN(C=O)C>[C:31]([CH2:32][C:22]1[C:21]2[C:25](=[CH:26][CH:27]=[C:19]([O:18][C:13]3[N:14]=[CH:15][CH:16]=[CH:17][N:12]=3)[CH:20]=2)[NH:24][CH:23]=1)#[N:29]

Participants

9

Reactant 6

HCID 5829N,N,N',N'-TetramethylmethanediamineHCID 6328Methyl iodideHCID 6367Acetyl chlorideHCID 9032Potassium CyanideHCID 19042873HCID 19042873, compoundHCID 19042905HCID 19042905, compound

Product 1

HCID 19042906HCID 19042906, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

Treatment of a cooled solution of N,N,N',N'-tetramethyldiaminomethane (0.854 g, 1.14 mL, 8.36 mmol) in CH2Cl2 (10 mL) with acetyl chloride (0.657 g, 0.59 mL, 8.36 mmol) followed by a solution of 5-(pyrimidin-2-yloxy)indole (1.268 g, 6.00 mmol) in CH2Cl2 (110 mL), gave after work-up: 3-(N,N-dimethylaminomethyl)-5-(pyrimidin-2-yloxy)indole as a yellow solid. This was treated with finely ground potassium cyanide (1.37 g, 21 mmol) and methyl iodide (2.94 g, 1.28 mL, 21 mmol) in DMF (70 mL) for 16 hr, and after appropriate work-up, 3-cyanomethyl-5-(pyrimidin-2-yloxy)indole was obtained as a light yellow solid, 0.98 g (65%).

Workup

  1. customgave after work-up

Sources & evidence

ORD record
ord-ccaca224c7824a07a7fb1407b14d0d4e
Source dataset
uspto-grants-1997_06
Patent number
US05637593

Reaction notes

Loading…