5-Methylpyrazin-2-amine → HCID 57504638, compound

HRID 1098159Notes

Reaction equation

HRID 1098159 reaction equation
ClC(N(C)C)=C(C)C.[Si:9]([O:16][C@@H:17]([CH2:21][O:22][C@H:23]([CH3:27])[CH2:24][O:25][CH3:26])[C:18]([OH:20])=O)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[CH3:28][C:29]1[N:30]=[CH:31][C:32]([NH2:35])=[N:33][CH:34]=1>C(Cl)Cl>[Si:9]([O:16][C@@H:17]([CH2:21][O:22][C@H:23]([CH3:27])[CH2:24][O:25][CH3:26])[C:18]([NH:35][C:32]1[CH:31]=[N:30][C:29]([CH3:28])=[CH:34][N:33]=1)=[O:20])([C:12]([CH3:13])([CH3:14])[CH3:15])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 3132155-Methylpyrazin-2-amineHCID 6407921-Chloro-N,N-2-trimethylpropenylamineHCID 57504639HCID 57504639, compound2×

Product 1

HCID 57504638HCID 57504638, compoundYield 52.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

1-Chloro-N,N,2-trimethylprop-1-en-1-amine (0.170 mL, 1.28 mmol) was added to a stirred solution of (S)-2-(tert-butyldimethylsilyloxy)-3-((R)-1-methoxypropan-2-yloxy)propanoic acid (Intermediate Y10) (250 mg, 0.85 mmol) in DCM (5 mL) at room temperature under nitrogen. The resulting solution was stirred at room temperature for 30 minutes. A solution of 5-methylpyrazin-2-amine (140 mg, 1.28 mmol) in DCM (5 mL) was added to the reaction mixture and the resulting solution was stirred at room temperature for 16 hours. The reaction mixture was quenched with water (20 mL), extracted with DCM (2×25 mL), the combined organic layers were dried (MgSO4) and evaporated. The crude product was purified by flash silica chromatography, eluting with 0 to 90% ethyl acetate in isohexane to afford the product (170 mg, 51.8%). 1H NMR (400 MHz, DMSO) δ 0.01 (d, 6H), 0.80 (s, 9H), 0.91 (d, 3H), 2.35 (s, 3H), 3.09-3.23 (m, 5H), 3.47-3.63 (m, 3H), 4.35-4.40 (m, 1H), 8.20 (s, 1H), 9.09 (s, 1H), 9.63 (s, 1H); m/z (ESI+) (M+H)+=384.43; HPLC tR=2.99 min.

Workup

  1. stirringthe resulting solution was stirred at room temperature for 16 hours
  2. customThe reaction mixture was quenched with water (20 mL)
  3. extractionextracted with DCM (2×25 mL)
  4. dry with materialthe combined organic layers were dried (MgSO4)
  5. customevaporated
  6. customThe crude product was purified by flash silica chromatography
  7. washeluting with 0 to 90% ethyl acetate in isohexane

Sources & evidence

ORD record
ord-3a030ab9ba844b4ab61832d4f52005ba
Source dataset
uspto-grants-2012_03
Patent number
US08143263B2

Reaction notes

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