N'-(3-Cyano-6-isopropyl-pyrazin-2-yl)-N,N-dimethyl-formamidine → 4-[4-Benzyloxy-2-(7-isopropyl-pteridin-4-ylamino)-phenylsulfanyl]-phenol

HRID 607329Notes

Reaction equation

HRID 607329 reaction equation
[C:1]([C:3]1[C:4]([N:12]=[CH:13][N:14](C)C)=[N:5][C:6]([CH:9]([CH3:11])[CH3:10])=[CH:7][N:8]=1)#[N:2].N[C:18]1[CH:23]=[C:22]([O:24][CH2:25][C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:21]=[CH:20][C:19]=1[S:32][C:33]1[CH:38]=[CH:37][C:36]([OH:39])=[CH:35][CH:34]=1>C(O)(=O)C>[CH2:25]([O:24][C:22]1[CH:21]=[CH:20][C:19]([S:32][C:33]2[CH:34]=[CH:35][C:36]([OH:39])=[CH:37][CH:38]=2)=[C:18]([NH:2][C:1]2[C:3]3[C:4](=[N:5][C:6]([CH:9]([CH3:10])[CH3:11])=[CH:7][N:8]=3)[N:12]=[CH:13][N:14]=2)[CH:23]=1)[C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1

Participants

4

Reactant 2

HCID 66808405N'-(3-Cyano-6-isopropyl-pyrazin-2-yl)-N,N-dimethyl-formamidineHCID 668085974-(2-Amino-4-benzyloxy-phenylsulfanyl)-phenol

Product 1

HCID 602048364-[4-Benzyloxy-2-(7-isopropyl-pteridin-4-ylamino)-phenylsulfanyl]-phenolYield 53%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of the product from Example 244C (56.2 mg, 0.259 mmol) and the product from Example 27A in acetic acid (1 mL) was heated under reflux for 2 h. The reaction mixture was cooled to room temperature and evaporated under reduced pressure. The resulting residue was triturated with methanol to provide the title compound (55.5 mg, 53% yield) as a beige solid. 1H NMR (300 MHz, DMSO-D6) δ ppm: 10.37 (s, 1H), 9.65 (s, 1H), 9.03 (s, 1H), 8.80 (s, 1H), 8.31 (s, 1H), 7.38 (d, J=8.09 Hz, 1H), 7.21 (d, J=8.82 Hz, 2H), 7.03 (dd, J=8.09, 1.47 Hz, 1H), 6.68 (d, J=8.82 Hz, 2H), 3.35-3.46 (m, 1H), 2.37 (s, 3H), 1.38 (d, J=6.62 Hz, 6H). MS (ESI+) m/z 404.2 (M+H)+ (ESI−) m/z 402.3 (M−H)−.

Workup

  1. temperatureunder reflux for 2 h
  2. customevaporated under reduced pressure
  3. customThe resulting residue was triturated with methanol

Sources & evidence

ORD record
ord-de0d17cf992e46c5b7b188a0826ac2a5
Source dataset
uspto-grants-2011_03
Patent number
US07915411B2

Reaction notes

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