Acetic Anhydride → HCID 136359250, compound

HRID 2189001Notes

Reaction equation

HRID 2189001 reaction equation
Cl.Cl.[NH2:3][C:4]1[NH:5][C:6]2[NH:7][CH2:8][CH:9]([CH:15]([OH:19])[CH:16]([OH:18])[CH3:17])[NH:10][C:11]=2[C:12](=[O:14])[N:13]=1.C(O[C:24](=[O:26])[CH3:25])(=O)C>C(O)(=O)C>[C:12]([O:18][CH:16]([CH3:17])[CH:15]([O:19][C:24](=[O:26])[CH3:25])[CH:9]1[CH2:8][NH:7][C:6]2[N:5]=[C:4]([NH2:3])[NH:13][C:12](=[O:14])[C:11]=2[N:10]1[C:16](=[O:18])[CH3:15])(=[O:14])[CH3:11]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 178469707HCID 178469707, compound

Product 1

HCID 136359250HCID 136359250, compoundYield 163.3%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

2-Amino-6-(1,2-dihydroxy-propyl)-5,6,7,8-tetrahydro-1H-pteridin-4-one dihydrochloride (0.1 g, 0.32 mmol) was slurried in acetic acid (3 ml). Acetic anhydride (300 uL, 3.2 mmol) was added and the mixture heated to reflux for 12 h. The reaction was concentrated and the crude material was purified by preparative RP-HPLC to give the final product as a white solid (0.096 g, 82%). 1H NMR (CD3OD) δ 5.15 (dd, J=2.4 Hz, J=10 Hz, 1H), 4.95-4.90 (m, 1H), 3.36 (d, J=13.6 Hz, 1H), 3.22 (dd, J=4.4 Hz, J=13.2 Hz, 1H), 2.16 (s, 3H), 2.09 (s, 3H), 1.85 (s, 3H), 1.26 (d, J=6.4 Hz, 3H). MS: ESI (positive): 368 (M+H).

Workup

  1. temperaturethe mixture heated
  2. temperatureto reflux for 12 h
  3. concentrationThe reaction was concentrated
  4. customthe crude material was purified by preparative RP-HPLC

Sources & evidence

ORD record
ord-33bfe5549aec4da1a6eb7a6392193fbd
Source dataset
uspto-grants-2012_12
Patent number
US08324210B2

Reaction notes

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