Methanol → HCID 25158502, compound

HRID 1714839Notes

Reaction equation

HRID 1714839 reaction equation
[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[NH:8][C:7](=[O:12])[C@H:6]([CH3:13])[N:5]([CH2:14][C:15]3[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[C:18]([CH3:24])=[CH:17][N:16]=3)[C:4]=2[N:3]=1.[C:25]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CO.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[NH2:1][C:2]1[N:11]=[CH:10][C:9]2[N:8]([CH3:25])[C:7](=[O:12])[C@H:6]([CH3:13])[N:5]([CH2:14][C:15]3[C:20]([CH3:21])=[C:19]([O:22][CH3:23])[C:18]([CH3:24])=[CH:17][N:16]=3)[C:4]=2[N:3]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 25158232HCID 25158232, compound

Product 1

HCID 25158502HCID 25158502, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

(7S)-2-amino-8-[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]-7-methyl-7,8-dihydropteridin-6(5H)-one (Example 1)(164 mg, 0.5 mmol) was stirred in anhydrous THF (1 mL) and triphenylphosphine (400 mg, 1.53 mmol) and methanol (0.2 mL, 4.94 mmol) were added. DIAD (0.3 mL, 1.52 mmol) was added dropwise and the mixture was stirred at room temperature overnight. The reaction mixture was loaded onto a SCX cartridge and washed with THF and methanol, then eluting with methanolic ammonia (7M). The crude product was further purified by MPLC eluting with 0-15% methanol/DCM. The title compound was isolated as a colourless foam after trituration and re-concentration from ether (113 mg, 66%); 1H NMR spectrum (400 MHz, CDCl3) δ1.39 (3H, d), 2.17 (3H, s), 2.25 (3H, s), 3.26 (3H, s), 3.75 (3H, s), 4.03-4.15 (2H, m), 4.66 (2H, s), 5.71 (1H, d), 7.57 (1H, s), 8.18 (1H, s); Mass spectrum: (M+H)+ 343.

Workup

  1. washwashed with THF and methanol
  2. washeluting with methanolic ammonia (7M)
  3. customThe crude product was further purified by MPLC
  4. washeluting with 0-15% methanol/DCM

Sources & evidence

ORD record
ord-5c29b00e57e042b09116a08ca241b927
Source dataset
uspto-grants-2010_09
Patent number
US07799781B2

Reaction notes

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