Dihydroxyacetone dimer → 2-Amino-6-hydroxymethyl-4-[4-(2,2,2-trifluoro-acetylamino-methyl)-benzyloxy]-pteridine

HRID 1695098Notes

Reaction equation

[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:21])[F:20])=[CH:12][CH:11]=2)[C:5]([NH2:24])=[C:4]([NH2:25])[N:3]=1.[O:26]=[C:27]1O[C@H]([C@H](CO)O)[C:30]([O-])=[C:28]1O.[Na+].C1OC(O)(CO)COC1(O)CO>CC(N(C)C)=O.O>[NH2:1][C:2]1[N:7]=[C:6]([O:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]([CH2:16][NH:17][C:18](=[O:23])[C:19]([F:22])([F:20])[F:21])=[CH:14][CH:15]=2)[C:5]2[C:4](=[N:25][CH:30]=[C:28]([CH2:27][OH:26])[N:24]=2)[N:3]=1

Participants

Conditions

Temperature: 40 °C

Procedure

Pyrimidine 61 (Example 43, 5.0 g, 14.1 mmol) is dissolved in dimethylacetamide/water (1:1) with sodium ascorbate (2.85 g, 14.4 mmol). Dihydroxyacetone dimer (2.57 g, 14.3 mmol) is added and the reaction mixture is heated to 40° C. while air is bubbled into the reaction mixture. After 4 h the reaction mixture is poured into 250 mL of H2O, and the formed solid collected by filtration. This solid is redissolved in CH2Cl2/MeOH (3:1, 500 mL), and dried over MgSO4. The crude product is adsorbed on SiO2 and purified by flash column chromatography using CH2Cl2/MeOH (20:1).

Workup

customis bubbled into the reaction mixture
additionAfter 4 h the reaction mixture is poured into 250 mL of H2O
filtrationthe formed solid collected by filtration
dissolutionThis solid is redissolved in CH2Cl2/MeOH (3:1, 500 mL)
dry with materialdried over MgSO4
custompurified by flash column chromatography

Sources & evidence

ORD record: ord-368e01af6d9d4c7c836480b10d3d3f80
Source dataset: uspto-grants-2012_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08163479B2

Reaction notes

Loading…