Sodium Hydroxide → HCID 178520003, compound

HRID 1056846Notes

Reaction equation

HRID 1056846 reaction equation
Cl[CH2:2][C:3]([NH:5][C:6]1[S:10][C:9]2[CH2:11][CH2:12][CH2:13][CH2:14][C:8]=2[C:7]=1[C:15]([NH2:17])=[O:16])=O.[OH-:18].[Na+]>>[OH:18][CH2:2][C:3]1[N:17]=[C:15]([OH:16])[C:7]2[C:8]3[CH2:14][CH2:13][CH2:12][CH2:11][C:9]=3[S:10][C:6]=2[N:5]=1

Participants

3

Reactant 2

HCID 14798Sodium HydroxideHCID 699491Sbb029873

Product 1

HCID 178520003HCID 178520003, compoundYield 25%

Procedure

The 2-(2-chloro-acetylamino)-4,5,6,7-tetrahydro-benzo[b]thiophene-3-carboxylic acid amide (20 g, 0.073 mol) in 150 ml of 1.5M-NaOH solution was refluxed for 4 h. The reaction mixture was cooled and filtered. The filtrate was acidified (pH=5) with dilute hydrochloric acid to give solid material. The solid was filtered, washed with water, and dried to provide 2-hydroxymethyl-5,6,7,8-tetrahydrobenzo[4,5]thieno[2,3-d]pyrimidin-4-ol (4.5 g, 25%) as yellow solid. 1H NMR (400 MHz, DMSO-d6): δ 1.70-1.80 (m, 4H), 2.68-2.75 (m, 2H), 2.80-2.88 (m, 2H), 4.35 (d, 2H), 5.61 (t, 1H), 11.95 (s, 1H); LC-MS: [M+H]=237.2 m/z.

Workup

  1. temperatureThe reaction mixture was cooled
  2. filtrationfiltered
  3. customto give solid material
  4. filtrationThe solid was filtered
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-8aab82615aa6445b9ec9ff21e6cb837d
Source dataset
uspto-grants-2016_07
Patent number
US09399647B2

Reaction notes

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