4-Hydroxy-but-2-ynoic acid ethyl ester → 1-Hydroxymethyl-5H-pyrimido[2,1-c][1,4] benzoxazin-3-one

HRID 126748Notes

Reaction equation

HRID 126748 reaction equation
[NH2:1][C:2]1[CH2:3][O:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C([O:14][C:15]([C:17]#[C:18][CH2:19][OH:20])=O)C>C(O)C>[OH:20][CH2:19][C:18]1[N:7]2[C:2]([CH2:3][O:4][C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=32)=[N:1][C:15](=[O:14])[CH:17]=1

Participants

4

Reactant 2

HCID 108554684-Hydroxy-but-2-ynoic acid ethyl esterHCID 128734192H-1,4-Benzoxazin-3-amine

Product 1

HCID 202879311-Hydroxymethyl-5H-pyrimido[2,1-c][1,4] benzoxazin-3-oneYield 72.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the compound of formula II, 3-amino-2H-1,4-benzoxazine (10.7 g, 72.1 mmol, described in Example 3) and hydroxymethylacetylenecarboxylate ethyl ester (9.7 g, 75.7 mmol) in ethanol (100 ml) was allowed to stand at room temperature (20° to 24° C.) for 6 days. The resulting precipitate was collected giving 12.03 g of the title compound as tan crystals with mp 235°-237° L C., the mp remaining unchanged or recrystallization from ethanol. The title compound had IR(nujol)3130, 1640 cm-1 ; NMR(Trifluoroacetic acid)δ5.2 (s,2H); 5.3(s,2H); 7.6(m,5H); Anal. Calc'd: C, 62.60%; H, 4.38%; N, 12.17%; Found: C, 62.32%; H, 4.24%; N, 12.17%.

Workup

  1. customto stand at room temperature
  2. custom(20° to 24° C.)
  3. customfor 6 days
  4. customThe resulting precipitate was collected

Sources & evidence

ORD record
ord-f68cb225d5bd4e9ea0444379aa24da3d
Source dataset
uspto-grants-1981_03
Patent number
US04254121

Reaction notes

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