Trimethylamine → HCID 11333667, compound

HRID 380442Notes

Reaction equation

HRID 380442 reaction equation
[CH3:1][N:2]([CH3:4])[CH3:3].[NH2:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][CH:11]=[N:12]2)=[C:8]([Cl:15])[N:7]=1>CN(C)C=O>[Cl-:15].[NH2:5][C:6]1[N:14]=[C:13]2[C:9]([NH:10][CH:11]=[N:12]2)=[C:8]([N+:2]([CH3:4])([CH3:3])[CH3:1])[N:7]=1

Participants

4

Reactant 2

HCID 1146TrimethylamineHCID 53603492-Amino-6-chloropurine

Product 1

HCID 11333667HCID 11333667, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Anhydrous trimethylamine was bubbled through a solution of 2-amino-6-chloropurine (10 g, 59 mmol) in anhydrous N,N-dimethylformamide (80 ml) for 30 min and the reaction stirred at room temperature for 12 h under a stream of nitrogen. The crude product was collected by filtration, dissolved in the minimum amount of cold water and the product precipitated out by the addition of acetone. The title compound was collected as a white solid (9.96 g, 74%)(m.p. 205-206° C.). (Found C, 41.8; H, 5.6; N, 36.9 C10H13N5O requires C, 42.1; H, 5.7; N, 36.8%). νmax/cm−1 3460 (NH2), 3320 (NH), 1640 (C═C), 1570 (C═C); λmax (CH3OH)/nm 316; δH (200 MHz, d6-DMSO) 13.40 (1H, br s, NH), 8.35 (1H, s, C(8)H), 7.10 (2H, s, NH2), 3.70 (9H, s, N(CH3)3); δC (50.3 MHz, d6-DMSO) 159.5 (C6), 154.9 (C2), 153.5 (C4), 135.0 (C8), 113.6 (C5), 37.8 (3×CH3); m/z (FAB) 192 (M+—Cl, 8%), 178 (MH+—CH3Cl, 72), 163 (MH+—(CH3)2Cl, 35), 149 (MH2+—(CH3)3Cl, 100), 134 (MH+—N(CH3)3Cl, 45).

Workup

  1. filtrationThe crude product was collected by filtration
  2. dissolutiondissolved in the minimum amount of cold water
  3. customthe product precipitated out by the addition of acetone
  4. customThe title compound was collected as a white solid (9.96 g, 74%)(m.p. 205-206° C.)

Sources & evidence

ORD record
ord-2b32e0f0c6214a368ceb0bdc647ab800
Source dataset
uspto-grants-2001_10
Patent number
US06303618B1

Reaction notes

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