Formic Acid → HCID 58980788, compound

HRID 1181372Notes

Reaction equation

HRID 1181372 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:23]=[CH:22][C:21]([NH:24][CH2:25][CH2:26][N:27]5[CH2:31][CH2:30][CH2:29][CH2:28]5)=[C:20]([O:32][CH3:33])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1.[CH:34](O)=[O:35]>>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:16][C:15]3[C:14](=[O:17])[N:13]([C:18]4[CH:23]=[CH:22][C:21]([N:24]([CH2:25][CH2:26][N:27]5[CH2:28][CH2:29][CH2:30][CH2:31]5)[CH:34]=[O:35])=[C:20]([O:32][CH3:33])[CH:19]=4)[CH:12]=[N:11][C:10]=3[CH:9]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 284Formic AcidHCID 58980893HCID 58980893, compound

Product 1

HCID 58980788HCID 58980788, compound

Procedure

A solution of 6-(4-Chlorophenyl)3-{3-methoxy-4-[(2-pyrrolidin-1-ylethyl)amino]phenyl}thieno[3,2-d]pyrimidin-4(3H)-one (0.050 g, 0.1 mmol) in formic acid (88%, 2 mL) was heated to reflux, concentrated, and then diluted with aqueous sodium hydroxide (0.1N, 2 mL) to precipitate the product as a white solid (0.051 g, 100%). LCMS m/z 509 (MH+). 1H NMR (300 MHz, DMSO-d6) δ 8.50 (s, 1H), 8.10 (s, 1H), 8.00 (s, 1H), 7.95 (d, 2H), 7.60 (d, 2H), 7.43 (d, 1H), 7.42 (s, 1H), 7.20 (d, 1H), 3.82 (s, 3H), 3.78 (t, 2H), 3.30-3.50 (m, 2H), 2.40 (m, 4H), 1.70 (m, 4H) ppm.

Workup

  1. temperatureto reflux
  2. concentrationconcentrated
  3. additiondiluted with aqueous sodium hydroxide (0.1N, 2 mL)
  4. customto precipitate the product as a white solid (0.051 g, 100%)

Sources & evidence

ORD record
ord-66a63fcfae7842d48789b5e912ff7e53
Source dataset
uspto-grants-2007_10
Patent number
US07285557B2

Reaction notes

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