Ammonia methanol → HCID 90411445, compound

HRID 1754621Notes

Reaction equation

HRID 1754621 reaction equation
[C:1]([Si:5]([CH3:31])([CH3:30])[O:6][CH2:7][C@H:8]([CH2:19][N:20]1[CH:28]=[N:27][C:26]2[C:21]1=[N:22][CH:23]=[N:24][C:25]=2Cl)[C@H:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH3:10])([CH3:4])([CH3:3])[CH3:2].[NH3:32].CO>>[C:1]([Si:5]([CH3:31])([CH3:30])[O:6][CH2:7][C@H:8]([CH2:19][N:20]1[CH:28]=[N:27][C:26]2[C:21]1=[N:22][CH:23]=[N:24][C:25]=2[NH2:32])[C@H:9]([O:11][Si:12]([C:15]([CH3:18])([CH3:17])[CH3:16])([CH3:14])[CH3:13])[CH3:10])([CH3:4])([CH3:3])[CH3:2]

Participants

3

Reactant 2

HCID 21705897Ammonia methanolHCID 90411487HCID 90411487, compound

Product 1

HCID 90411445HCID 90411445, compoundYield 67%

Procedure

A solution of 49 (4.2 g. 8.65 mmol) in 60 ml of 6M NH3/MeOH was sealed in a 100 ml Parr bomb and heated with stirring for 20 hrs. The reaction was cooled and concentrated to a white solid, which was re-crystallized from 10% ethyl acetate/hexane to afford 2.7 g (67%) of 50 as white crystals. 1H NMR (DMSO-d6): δ 8.10 (s, 1H), 8.02 (s, 1H), 7.16 (s, 2H), 4.18 (m, 1H), 4.06 (m, 1H), 4.00 (m, 1H), 3.53 (m, 2H), 2.29 (m, 1H), 1.16 (d, J=6 Hz, 3H), 0.84 (s, 9H), 0.79 (s, 9H), 0.01 (s, 6H), −0.10 (s, 6H).

Workup

  1. temperatureheated
  2. temperatureThe reaction was cooled
  3. concentrationconcentrated to a white solid, which
  4. customwas re-crystallized from 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-7cd6e2c555054d0298b2e6dae4f0c174
Source dataset
uspto-grants-2015_10
Patent number
US09169256B2

Reaction notes

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