Formaldehyde → HCID 178473769, compound

HRID 1504087Notes

Reaction equation

HRID 1504087 reaction equation
[OH:1][C:2]1[C:3]2[CH:10]=[C:9]([CH2:11][CH2:12][NH:13][C:14](=[O:16])[CH3:15])[S:8][C:4]=2[N:5]=[CH:6][N:7]=1.C=O.[C:19](O)(C(F)(F)F)=O>ClCCCl>[OH:1][C:2]1[N:7]=[CH:6][N:5]=[C:4]2[C:3]=1[C:10]1[CH2:19][N:13]([C:14](=[O:16])[CH3:15])[CH2:12][CH2:11][C:9]=1[S:8]2

Participants

5

Reactant 3

HCID 712FormaldehydeHCID 6422Trifluoroacetic acidHCID 178474657HCID 178474657, compound

Product 1

HCID 178473769HCID 178473769, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

To a solution of N-(2-[4-hydroxythieno[2,3-d]pyrimidin-6-yl]ethyl)acetamide (300 mg, 1.26 mmol, 1.00 equiv) and paraformaldehyde (300 mg, 10.00 mmol, 7.91 equiv) in 50 mL of 1,2-dichloroethane at 0° C. was added CF3COOH (6 mL). The solution was stirred for 12 h at room temperature. The resulting mixture was concentrated under vacuum. The residue was applied onto a silica gel column with dichloromethane/methanol (10:1) to afford the desired 1-[3-hydroxy-8-thia-4,6,12-triazatricyclo[7.4.0.0-[2,7]]trideca-1(9),2,4,6-tetraen-12-yl]ethan-1-one (200 mg, 63%) as a light yellow solid. MS (ES): m/z 250 (M+H)+.

Workup

  1. concentrationThe resulting mixture was concentrated under vacuum

Sources & evidence

ORD record
ord-f677f2c32528429f96cc22cb23f315c6
Source dataset
uspto-grants-2015_12
Patent number
US09212190B2

Reaction notes

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